First off, I'm not a savvy investor, (forgive my ignorance) I have been trying to learn the ins and outs past couple years by reading on here and listening to podcasts. I own 3 properties, one of which is a paid off 1430sq ft SFH and has been a good income producing rental (rented out for past decade).
I own and live in a larger 2400sq ft 4/2.5 SFH and owe about $246k mortgage/(have 58 k on HELOC). I would like to downsize but I don't want to buy in this market, and I'm not sure I can qualify for a bank loan right now due to my business (main job) taking a hit past year from Covid and year prior from a messy traumatic divorce (long story). In any case, I have not been able to qualify for loans to do cash out refi or mortgage to buy a new smaller home for myself. I've considered moving back to my rental house (smaller, would work) but I'm not super crazy about the house (bad memories) and ideally, want to start fresh with a different new to me smaller place.
I also own a commercial property office space (1800 sf office) condo. I owe about 102k on that office condo and have a 10 year loan at about 4%, $1000 a month payment. The commercial property recently appraised at 300k. The property taxes there are high ($4000 a year, HOA is about $3000). I'm considering selling that as well, because I could rent a smaller space and have less overhead for my job (own my own biz). I tried to do a cash out refi on that but my application was declined by the bank due to reasons mentioned before.
Here are the scenarios...
Rent out my current home, move back to the paid off rental (smaller, would help me save $$, less expensive to maintain). My current home really needs at least 20k (maybe 30) of remodel and repairs to be in good shape to sell for top dollar or be ready for renters to pay at least $2500-3000 a month rent.
Sell my current home, move back to paid off rental, stash the cash until home prices come down again and buy something else later.
Sell my rental, take huge capital gains hit and recapture of depreciation (been a rental since 2011). (bought it for 159k, it should sell for around 350k or more) and stack the cash for later when the bubble bursts and be ready to buy something else then.
I'm putting a lot of pressure on myself to sell something now, as I'm worried that the bubble will burst and I'll kick myself later. But my main goal is to maximize my investments here and since I'm 55, have a good return to help me in retirement. And I'm worried that my office condo (commercial) will lose value in the next few years.
So....(sorry, I know this is long and convoluted!) what am I not seeing as possibilities in this picture? Ultimately, I want to make the best money moves WITHOUT emotions clouding my decisions. I feel like there are so many options it's dizzying. And I realize I'm fortunate to have these options, as I know many others are struggling in bigger ways, but I'm really not sure what the best money move is here. If you made it this far....THANK YOU for reading and for your thoughts. :-)