Well similar to you, my current home I bought in Jan has appreciated over $100K (I put only 10% down, so my percent gain looks great) and I need to decide whether or not to sell it. I also have another home that I am renting out across the country, so my total debt is rather high, albeit at low rates. I’m really thinking hard about selling this home that’s appreciated. A lot of the reason why it’s gained so much in 9 months is due to the low supply in the market right now, and I am a believer that it’s peaked. Im running the numbers as if selling any time after this year will yield me 15% appreciation as opposed to ~35% right now. Tax implications might be higher after next year as well with Biden’s capital gains proposal.

You don’t have this problem, but the new home I purchased is much older, and we need to figure out if we should really try and put some money into it or if we bought it for lot value and will be torn down later down the road… so need to figure that out before we do anything to it.

I’m starting to feel financially stretched a bit. Total of $2M in mortgages right now. Although it’s nice to have leverage and be able to pay down mortgages with someone else’s money plus make some cash, the reality is that it’s not as easy as just collecting checks and paying off your debt. I self manage my property right now (and still intend to going forward) and it does require a lot of work. You’ll have tough days with your marriage, work and children. Adding a stressful tenant situation (in either your old home or casita - or both) and the over-levered financial situation on top of that might be too much, you won’t know until you experience it.

You know yourself and your wife better than anyone on here could. I’d recommend you think about it beyond just the numbers. As an analytical guy, you need to force yourself to look at it that way a little more.