Over the past several years I have incrementally fixed up each of my properties (after taking over from the PM). I have a 2 family that has not gotten the full treatment yet. Has one long term tenant. Half the shingled roof is on it's last legs and the other half isn't much better. An estimate 2 years ago for 1/2 roof was $4000.

One furnace in the attic is way old army green affair (from the 70's?). The other I have had the blower motor replaced 2x and the frame is rusting out. The heating guy always tells me that it will collapse on itself any day (that was over 3 years ago).

I have converted to pex for the 1st fl and the circuit panels are updated.

I collect 1100/ mo in rent. I don't think I want to own property more than ten more years. I thought the other day, as a stand alone property it's probably not worth holding onto and carrying these expenses (not to mention updating the units when the time comes). I might get 70k for it now, it's not in an ideal location and has no desirable features (driveway, etc).

I have another 2 family with 3/4 brs that is harder to deal with that I've always thought would be the "first to go" but it cash flows well. The 2 family with the ten yr smoking catlady tenant is one where I had to replace both furnaces in the same year. So I know how painful that is to absorb. Guess that, and knowing what roofs cost made me think about where I want to get to and if this one make sense to cut loose now.

Sell them both on 1031's.

Find an industrial park in a smaller town and get 2 or more lots next to each other (with or without buildings). Exchange each current property into a separate lot or lots (depending on the numbers). If the buildings don't sell at the same time, the separate lots can be adjusted on closing times to make it work.

If you get the right area, you might be able to get a good sized lot (here I can get a lot of about an acre pretty cheap). String as many lots together as you need to make the numbers work.

As an example, I've got about 8 lots in a row on the same street locked up. Bought the first one and have options on the rest. So I can just exercise the options as needed.

Sell your two family. Don't even replace the roof unless you want to open up your selling market to owner occupants and noob investors. Here selling with a bad roof is going to attract pro investors only and limited attraction to an owner occupant.

Owner occupants pay higher prices and some think they can do the work themselves. It may or may not be the same in your market.

A good roof in S Fl is critical to getting HO insurance. So with a roof in bad shape the buyer has to have the funds to change out the roof within 30 days of purchase to keep the insurance (it's a requirement) and there is only one co that will insure in that circumstance. Find out the added value if the roof is sound or newer, if any.

I have had the same questions dealing with rentals that I want to let go and re-invest in something else. I decided that when my rentals turn over 80 years of age (pre 1920's), their design and construction was too old and not sound enough to withstand the years, maintenance, earthquakes or fires.

Sometimes over my ownership I'd fix up the property unit by unit as it became vacant. Or all at once I'd change a component in the entire structure -- like new windows.

Two years ago a friend with an extra single family house and a duplex was going to sell them both quickly and cash out. If they did this, they would net after taxes around $500K. Instead we sold the house and used some of that money to fix up the duplex. We got new tenants, good ones that paid the rent early via online payments. We also placed a manager to take care of any problems. So now my friends had lots of money left over from the sale of the house and a duplex making them a great income.

It is a challenge to get replacement properties. In a balanced market, I just turn to a property that I have an option to buy. The option properties ran low about three years ago when things started to shift to a sellers market. The market is simply crazy now with less than half the number of places available than at the start of the pandemic

So last year I attempted 4 different 1031 and was able to complete only 3 of them - that is find replacements on three of the four. When you don't pick up a replacement property the 1031 company will hold the finds for 180 days and then return them to you.

In my successful exchanges I shifted to lower management type properties. Oil and gas rights, timber, a NNN lease commercial property. Many of these price points were inflated have been even more so now. So for me it came down to quality of life.

Toilets and tenants is not the end. It is only a tool to reach the end.

My end - more freedom. How do you babysit a gas well? You have to check your online banking once a month. A NNN lease place? Those cheap folks still mail checks just so that they can float money.......figure that out, a fortune 500 company making money off of floating money - that is efficiency by being non-efficient. As for timber, you get a cutting every 10 or so years. The 20 acres ran me 1,700 an acre and I estimate we have $5,000 in just Cherry that is ready for 2021 or 2022.

With the money I am suppose to be getting back from the 180 period, I think it is the end of this month or early next month......maybe I will write some small notes.

I believe in the velocity of money will make you money. I know there were experts that will tell you buy and hold.......for me it is buy hold until paying it off and then exchange it for the next hot thing. That is tough now as the government has pumped so much money into the market place.

Ray n Pa there are Amish, never thought they'd be looking for financing. I think they are competition for buying up land. Each family needs their own parcel.

There are tons of failed nurseries and garden centers around.

Cuomo just announced a whole bunch of solar projects. Not sure what impact that has on the area. I suppose if the new grid gets built then solar farms will pop up along it.

Robert everything I have is over 80. I've proceeded much as you describe over the past bunch of years. Updating units, doing windows, roofs, heating systems, water heaters, pex etc.. I just stopped and thought I have this last one that has been low input and I look forward and realize it will require capital, and how does that fit with what I want to do in ten years. I'm already where I want to do less house calls (and there are fewer with the improvements I've made).

If I sell, the loss of cash flow does reduce my ability to save and accumulate funds. My portfolio is all about cash flow, not appreciation. Maybe a lake house- Ken did you go for that lake rental you mentioned a while back?

Amish tend to be all cash folks and they don't like dealing with banks.

In their culture they feel very obligated to keep their word and pay on time.