Hello everyone! I’m revisiting this thread and updating as things have progressed quite a bit. I feel good about my new plan but always love to hear some other ideas or counterpoints.
So, long story short: Things have come to a head with one of the mountain rentals (“Zell Ct”).
Essentially, it’s deteriorating quickly, winter was not easy on it. There is quite a bit of wood to replace (It was built In the 60s). I need to scrape, sand and paint literally every exterior surface of the house and large deck along with roof repairs. On top of that, the tenants are turning into real dirtbags, there are six aging vehicles parked in front (some on blocks), sheriff has been called out multiple times, all kinds of interior problems, can’t even get to the deck repairs yet due to the excess amount of junk stored above and below the deck. There is no good management up there and very difficult to find handymen. The great cash flow is just not worth the stress, it has to go! I’ve already given them 60 days notice (holdover tenancy).
The other mountain rental (“Arth Dr”) isn’t so bad, I already finished yearly repairs and it has a decent tenant although I feel I will want to get out of this eventually as well (another huge old deck with yearly wood replacements and deck re-stains).
1. I looked at 1031 into DSTs, Upreits etc and ultimately realized I have no interest in them. I’ve found I can manage my own investments well with excellent returns and don’t want to hand it all over to someone else who I don’t know and have no ability to control things.
2. I’ve calculated every possible combination of 1031 exchanging “Zell” or both mountain properties into other types of like-kind investments and with the interest rates it never makes any financial sense. I’ve felt very “trapped” with these properties.
3. Ultimately I started to consider paying capital gains tax and here are the broad strokes of what I came up with: “Zell” has to go no matter what, my plan is to pay the tax on this (multiple calls with CPA to confirm the details), then with the proceeds I can pay off my auto loan (5.5%, easy win) and then also pay off “Arth”. These moves will actually increase my monthly cashflow a bit (when considering extreme maintenance on “Zell”) while greatly reducing stress. The bigger perk is that with “Arth” payed off, when I’m ready, I can do a 1031 with that into cash offers on other lower maintenance properties as interest rates will not be a concern. Being “locked in” to those properties has been a significant source of stress.
4. So, to summarize, pay the capital gains on first sale (Zell), then I can avoid taxes on the second one (Arth), gain freedom, time, flexibility, reduce stress and gain a little cash flow. Yes, perhaps it's counter-intuitive to pay off a 3.5% investment mortgage on Arth with higher ROI options however these gains will be guaranteed (I have some other paper losses I can utilize to reduce the taxable burden on the increases cash flow) and provides me with paid off 1031 flexibility.
I've done IRR and cash flow calculations on all my options (out of scope for the post I figure) and also considered just dumping taxed funds into SP500, bonds, HYSA, REITs and other options but I want safe, stress free, low risk cash flow with this capital.
What do you think about the general strategy? Thank you ahead of time for any replies!