For instance, a couple months ago I came across a distressed property on the mls.

Its better to under commit and over deliver.If you know the HS person fairly well I would just give him a call as a heads up you bought the place.

We did not end up doing it (for which I am very grateful now because I knew nothing about renting at the time and now think it would have ruined me for ever renting in the future) however it planted a thought in the back of my head that drove me to do some reading now in 2021. 

We had similar instances occur where the tenant tries to pull their notice due to personal reasons.

However, I've been looking on the MLS-linked sites  at multi families in San Antonio and running my numbers, and I'm wondering if this sentiment that MFs are better than SFs in San Antonio holds.For instance, the quads I'm seeing have downpayment of over 120,000 and up (assuming 20 % down), and cash flowing $800 per month.

I know there are many options and I will talk to a lawyer and CPA, but I'm trying to wrap my head around things first. 

Don't get in over your head.

If you want higher limits, many times your only option is to buy an Umbrella policy.So the umbrella policy etc would be for once the unit is ready to rent then I would put it on before a tenant moved in and change from vacant policy to whatever was the correct policy to have in that instance. 

If we hate landlord-ing we can sell it, but scaling to more is not out of the question once we feel we're not in over our heads.

When I initially started I had a really hard time wrapping my head around the cash-out refinance, I thought I cleared it up, but maybe not?