Work with the local experts- talk with local zoning officials, engage architects, and reach out to contractors to understand the cost and feasibility of your project.Run your numbers- do some forecasting and layout some financial models to project costs, revenues, and returns.Make sure you are utilizing your team- aforementioned real estate broker, financial advisor/ CPA, and lawyer and others as you go.Best wishes and good luck.

STR management is a highly local, hands on business and their business model just doesn't make sense.

@Brian Jordan @Dustin Heiner Interesting contrast in your approaches; however, it is obvious to me that you each have solid, well thought-out business models. 

Our company, Pleasant Valley Containers, has 4 home models that are move-in ready for under $80k.

The tenant is not as much focused on rent when they are strong regional to national in nature but the best spot they believe drives the most sales and profit annually.It's the lesser quality smaller tenants that are more sensitive to rents because their model is not often proven with scale or over time as much.So you have to know what you are buying and what to do with it.I buy same stuff for cash but I am the GP on the syndications and my LP's put in minimum 200k per deal as accredited investors.To convert the bank to medical would be very expensive.

It's a more heavy intensive property management syndicate model that I have no interest in.  

I've got 1 STR in Longmont and a handful of clients/investor friends around the Northern CO region running the STR/MTR model.

Most notable cost basis, debt service, cap ex schedule, accounting, checking account oversight for ease of transactions, property tax tracking and trends, custom KPIs and modeling. 

I like the fixer Jay Decima model, where he sells some of his assets on seller financing, avoiding the big cap gains hit, and creates mailbox money.That would be a conversation with a qualified financial planner.All the bestGino

My goal is to focus on purchasing small multi-families to self manage with a STR/ MTR hybrid model in the Central FL market.