Call the Sheriff dept and ask how long he'll stick around as the deadbeat packs up.

While reading your post I was thinking "sell the Cali properties", but with 3-4% interest rates (and I'm assuming those are long term fixed rates) you will be best off to cash out refi (non-tax event) and use those funds to buy multifamily.

.- Going rate for TH and individual rooms- Demand and saturation levels (how long does it take to rent), length of stay, etc.- Other market trends about the areas TH and individual room rentability - Frequency of renting versus selling in the areaI look forward to the insights you all share!

I plan on doing long distance investing since I’ll be deploying to Japan soon! 

Numbers in FL are not looking great with insurance/taxes/HOA fees/etc for cash flow but willing to  focus more on just breaking even (or close to even) and having significant long term appreciation.Option 2: take the cash, pay 20% long term capital gains and wait as market continues to dip for a prime buying opportunity.Would greatly appreciate insight/advice from those much more experienced and knowledgeable than myself.

This means you could do 0% down on a $1M, $3M, $5M, etc. property as long as it's a residential property with 4 units or less. 

With most of the mortgage brokers I know, there isn't a clause saying that you cannot rent out your second home as a vacation rental as long as you are still intending to use it personally.

As you are pointing out - the expenses will all hit at some point if you own for long enough.If you buy a house that needs a new roof and a new furnace within a year... then you need to budget for those expenses in a year. 

Either that wall is taking on a load and the studs are bowed or they installed them to long and bowed them in place.

Real estate is supposed to appreciate long term at the rate of inflation so you're not better off over time with just that.