Aim for a path that benefits the current tenants if it's worth it.

You might have other options to explore to drum up liquidity (HELOC, Margin Loan, Policy Loan, etc) that can supplement your HYSA in the DP.

If It is a wholesale DSCR lender that also does TRID loans, they might require a bit more paperwork, such as a VOM, mortgage statements for properties currently owned, and credit supplements on mortgages on your credit report.

Looking to rent for $175/night min and total estimate is $100k for the build, aiming for 20% CoC.Any pitfalls/advice for this uncharted territory?

When I first bought this rental property, I wasn’t aiming to become an expert in real estate or accounting—I was simply looking for a passive investment.

Our portfolio currently cash flows, but cash flow isn’t our top priority right now since we plan to use this portfolio to supplement our retirement in 12 years when I leave the Army.My biggest challenge is committing to an out-of-state market.

Quote from @Xavier Perera: Aim for a four-plex.

Has she even received a supplemental tax bill yet? 

Questions/opinions on: (1) one property or several, and (2) whether to buy outright or put large downs and then supplement with mortgages.

I am not preticuarly brand new to real estate as I've done 1 house flip before and 1 brrrr here locally to me.To begin, I’m aiming to tackle two single-family BRRRR projects in the Jackson County, MO area.