Some good questions for him to ask each potential company are:- how long have you been in business- what is your fee (be specific on the number of properties involved and if it's forward, reverse, etc)- where is your operations staff located (ie where will be funds be)- what type of account will my funds be held in? 

Legaly all rent by the room operations are in violation of hotel, zoning, and rooming house regs. 

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Do you have the professionals you need to start an LLC, do the proper real estate/tax accounting, solid contractors to rehab or prepare the property, and a property manager to handle the day-to-day operations? 

In order to get a line you would need 2 years of operations, and have an operating company - like a property manager or a construction company.

These two things can do worlds of good for a high net worth investor looking to maximize tax- deferred/tax-free growth and minimize general taxes from operations.

Operating an LTR is quite different from managing a short-term rental , so I'd recommend focusing on mastering one strategy before expanding your portfolio.

hmmmm, raising capital for operations vs each property?

I hope this question makes sense as this is our first year filing and our first full year of operation. 

If the seller is trying to avoid legal issues with the city for illegally operating a property I would get out of that.