The direct appeal is to lenders (primarily commercial lenders closing in the $5M-$100M territory).

This year for 2025 my wife and I have made it a goal to improve our financial literacy to purchase another investment property.

I think my main pain point is underwriting the property as it is and then seeing what it could be and then making decisions on if it's worth and how those decisions are made.  

This ensures you have a proof of concept to show the commercial appraiser.  

Don't depend on Aircover.Homeowners policy will not protect you if your renting as a STR.You need the correct STR policy to protect your property.

I have flipped multiple properties mostly land and SFH.

I just listed my last property for sale, a fourplex in Pocatello, because now I focus more on commercial RE and syndications to be a true passive investor and not deal with tenants and repairs.

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!

I spent a decade in advertising, before founding and running a custom wood shop for another decade, so 'm pretty good at the self-promotion.I agree with you that the more gorilla approach would be most effective and that's actually what i've been doing – calling RE agents in my service area with active listings, introducing myself to property managers and leasing agents...To answer your question, I will have to handle the work myself for 6-12 months to build out the SOPs and field service management systems, but I have a lot of relationships for those looking to "do the work".I'll check out the meet up and would love to grab a cup of coffee, I'll shoot you an email.

Wondering also if there are lenders that would have an appetite for this type of property?