I’d really appreciate any insights, whether there’s anything I missed, any places you’d avoid, or any tips for STRs in this market.

I wouldn't consider it a heavy negative unless the street is super tight and parking is hard to come by or if the street is very steep/busy.The more desirable dense city neighborhoods it's almost kind of expected and off street parking would be considered a luxury rather than a necessity.If you get out into the suburbs I would say it's more of a big deal since more rentals have off street parking or a garage there.

Has anyone done something like this before and has insight/tips/advice?

Bad management can tank a deal just as fast as anything else.Did you fire the manager and work on finding new management?

Thanks for the quick reply and advice!

Here’s some context: Property 1: >$100k in EquityValue: $325kDebt: $220k @ 2.88% (30-year fixed)Property 2: >$70k in EquityValue: $325kDebt: $252k @ 3.38% (30-year fixed)Extra considerations: - I have $15-20k liquid to use for any of these deals- My current job is relatively stable, but not high-payin- Current properties in TX, living in NY, looking to invest in Mid-West (crazy, I know)- No other debt obligations besides the two mortgagesUltimate goal/timeline: Though a bit ambitious, I’d love to build up the portfolio to 10-20 units in the next two yearsI understand that any/all replies aren't financial advice; all ideas welcome for information purposes. 

Thank you for the reply @Dave Meyer, it's not everyday that I get to converse with BP Royalty. 

Do you have any tips on how to approach and structure deals with private lenders for scaling?

4) How fast can you move if the agent brings you exactly what you are looking for?

Better rate would help your cash flow.i would pass,  more relevant is I recommend you pass on this purchase.good kuck Hi Dan, thanks for the reply.