@Jenny Yu sorry to hear about your experience, we own and operate 51 units we own and manage for other clients in Jacksonville and Orlando.

Is it Leasing, Property Management, Vendor Management, Operations, Finance, Accounting... 

Hey Dan, renting to a sober living operator can be a great idea.

And many hotels don't have 24 hour desks or 24 hour service.I don't get why all these newer regulations expect STRs to operate to standards that aren't even required of hotels with full-time staffs. 

With insurance rates going up, best to find areas with the lowest operating cost.

From my understanding, as long as you intend on doing a STR when you close, there are no rules against changing your strategy after closing, especially if you find that something else is more profitable.So in our case, the lender determined an STR would bring in ~$3500/month (with all of their conservative factors), but now that we operate it as a huge 3300 sqft Co-Living property, it actually brings in $7000/month.

It's easier to scale with multifamily properties due to income potential and operations.

You can build your own team i.e. title co, insurance, pm, contractors, handyman,process server, lender etc.... or you can find an operator who can get you going in that market while simultaneously building out your team.Section 8 housing is a great way to ensure consistency with rent payments however not all tenant who have HCV pay 0%.

But the "art" really only comes with time in market and a deep understanding of both the market and the operations of assets.

Then you specialize or hire legal, operations, finance, investor relationships, concept, deal analysis, Which investment level your at determines what experience you need.