I feel like having such a low payment and rate make it stupid to choose selling the house, but since I haven't been in this position before, I thought I'd ask here. to d The other consideration you would want to consider is your VA entitlement if you are hoping to buy the next house with a VA loan.

I accepted a tenant into a B class rental a few years back who was making low 6 figures at the time as a union boiler-maker but had NO CREDIT SCORE!

There are a lot of hotels right now that are failing and going under due to low cash flow -so its a failing hotel.

The only caveat with that loan is that you'll need to purchase in a low to moderate-income tract. 

I haven't filed a claim all these years but insurance is for the what-if and to be used for the high-ticker items, but chances of damages exceeding the 5% is low.  

I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?

I made a low offer and it was accepted.

I have purchased the following books:ABCs of Buying Rental Property The ABCs of Property Management The ABCs of Real Estate Investing The Advanced Guide to Real Estate InvestingThe Book on Investing in Real Estate with No (and Low) Money DownWhat order do you recommend reading them in?

If you are very conservative purchase a fixer upper so you can force equity and hopefully have a low enough payment so that you can LTR the property or even sell for profit should the STR avenue not work. 

I sent an invite to a prospective applicant that qualified and Looked high and low for the invite form with some additional notes to the applicant only to find out that it is not even on the platform at all, anywhere but in an email confirmation I received.