I am looking at investing for my future not right now but I am wanting to make around 250 in cash flow.

Someone who is a STR specialist should have referrals to all of the tools the buyer needs such as design, maintenance, cleaning, management, etc.If someone uses me and wishes to self manage, I will still set them up for success.

You can't charge a deposit, rent, or anything else.However, you are allowed to enforce rules regarding noise, keeping the animal under control, cleaning up after it, etc.

Determine a goal what you want from the investment property , meaning what's the monthly cash flow you are looking for $250,$300, $350 etc..or is it 8% to 12% of your total capital invested. if the number works then it's a very good start. let me know which neighborhoods you are looking in. 

Rented rooms to friends and cash flowed from day 1.

The loan would be based off of the cash flow or return on investment of the property itself instead of your personal income.

Low Income affordable housing - tend to be rougher on the units, they get a basic 1 tone paint, inexpensive flooring package, no disposal or ice maker or dishwasher - Deep Clean and Safety is my concern. 

If you are solely interested in the cash flow you can continue to pay extra towards the mortgage and if your situation changes refinance it as a 15 year mortgage at a lower rate on a lower rate which will lower your payment and increase your cash flow.

Are you looking for cash flow or appreciation?

I would starting by have a clear goal for your investment - is it cash flow, COC, ROE?