There's a common belief that your tax person should also be an investor themselves.

A mortgage lien being the most common one.

And this all gets worked out before the contract is actually accepted.Why Your Agent Matters: Common misconception that agents are door openers - to be fair most act like it.

Eventually, I’d like to start using the cash flow to pay myself and work toward replacing my day job income.

Overland Park, KS vs Kansas City, MO) Very landlord friendly, worst case eviction is usually 8 weeks + $500 + lost rent (cannot comment on individual cases and this is not legal advice) Large diverse metro area - variety of jobs, companies, people can have a career in KC.

I agree that DealCheck (or the BP calculator) does not provide enough tools or functionality to analyze those types of transactions (yet).But I would argue that it does a great job at analyzing more traditional buy & hold SFRs and multi-families, as well as flips and rehab projects. 

Quote from @Paul Gupta: Hi, in California, For jobs requiring a license, there was CSLB (contractor state licensing board) which would give either a General Contractor license, or specialty licenses by trade (~60 specialties such as concrete, welding tile, ) https://www.cslb.ca.gov/about_us/library/licensing_classific...My Q: does Maryland and DC area have similar requirements? 

i would:-get the highest paying W2 job you can-save up enough to buy a house hack-house hackwhile you continue to learn and consider the other possibilities you mentioned.

I work a full time job at a wood shop building custom cabinetry.

I do relatively well in my day job by today's standards but my hourly rate for self managing is closer to that of a surgeon.