As a beginner, many lenders are likely going to require a personal guarantee (often referred to as a PG). 

The Route 1 Corridor in PG County (Hyattsville - College Park) is a great location for this strategy, with high demand for tenants, a diverse mix of property types (many with basement walk-outs), and relatively affordable prices.

You can’t require a PG when lending to a retirement plan.

To answer your 1st question, your monthly payment will likely be higher in a year but it’s quite possible if not likely prices are down and inventory is up in the near future so it’s kind of pick your poison.To answer the 2nd question with your budget you’d likely be getting a fixer in Riggs park/Brentwood, I’d look on the route 1 corridor in PG county (You can get a fully renovated single family detached homes in your budget.) 

You could also look in moco and possibly pg and nova (not sure) about getting an adu. 

As far as 203k rehabs it’s super hard to find deals with enough equity to make that happen right now however there are still some pockets of D.C. and western pg county and some parts of Baltimore where you can get some equity.

I know there comes a point where you have to "poop or get off the pot" (using the PG version here) and there's a lot of learning with experience, but how do I know when I'm there?

These lenders can include:- Local Banks & Credit Unions (typically lowest interest rates, but capped to 25-yr ams and usually 3, 5, or 7-yr balloons)- The "Secondary Market Lenders" who are going to require a PG usually, but will offer that 30-yr fixed, as well as the ever-so-sought after 5 - 10yr Hybrid loans (I/O during first 5-10 years, then converts to a 20-25 yr fully amortizing loan [no balloon!]).

I bet there are other counties too in Texas that have methods where you can get these records for less than $1/pg.

My question is why would I choose the option to get the loan in the business name with my pg, vs only getting in my name with the same pg.