@Rachel Seymour-NewtonIf the smaller property is a strong deal with solid cash flow and tenant demand, it could make sense to buy now and start gaining experience.

Some may skip trace for you and giving you calling and text message integration.One thought is in my experience probably 80% of the properties don't go to sale, the first date they are posted. 

First and foremost, I'm in Minneapolis / Saint Paul, so I'd like to know if you have any suggestions for 1) what investor meetups I should attend, and 2) recommendations for building my team (CPA, real estate lawyer, handyman / contractor, insurance broker, and agent (I have one but they don't seem to have much investing experience)).

If you've had experience with similar deals or have knowledge of the McKeesport market, I'd greatly appreciate your insights.Thanks in advance for your feedback!

I’d love to connect with like-minded investors locally and learn more about their experiences with HMLs.Thanks again for your time and help!

Looking forward to learning from your experiences! 

In my experience, there are several avatars here. 

@Marc Shin We're funding cash out refis for a lot of our most experience BRRRR clients right around day 91 (to pass 90 days of title seasoning) where we get the process started (appraisal, title, application, etc) around day 60  (plus or minus) when they have the place fully renovated and at least listed for rent (we'll use appraisers opinion of market rent to calculate DSCR). 

If you will be a large equity partner or if you hold the experience to do the deal, the lender will likely want you on as a guarantor.

But experiment and see what happens in your market with your specific property.