I would just note as a lender - its going to be much easier to find financing (and have more options) if the property is more of a traditional SFR / residence versus a cabin or creative type tailored STR property. 

Some contractors have insurance, some are 1 man band with no overhead, quality of work factors into cost, level of finishes.We created a calculator for our clients to use here in Chicago, specific to our renovation pricing, but even that is just a guess based on some assumptions.If you can find a quality general contractor, pay them like @Bruce Woodruff mentioned, and it will make your life so much easier...you may eat into some of your profits, but being able to rinse and repeat with someone you trust is priceless!

It is also far easier and more cost effective to scale by selling membership interest of an LLC or simply purchasing your real estate in LLC's where you raise money from friend's and family to serve as LP investors.   

That will make it easier for renting the long-term rental for sure because you can advertise the base rent, which is comparable to market rent, and then state that utilities are included for the utility fee.

@Michael Dooley  What is your target date to finish the rehab? 

I agree with previous poster that the areas around GVL may be easier to get into.

They’re easier to qualify for and will allow you to bypass personal income/asset tests.Let me know if you have any specific questions about Montgomery—I’d be happy to help.

To make sure the investment satisfies your financial objectives, establish your target profit margin.Decide how much money is needed overall for the transaction.

Also start going to meetups and do some exercises like picking a target market!

Plus, the seasoning of the company can make it easier to secure better credit terms or refinance quickly since lenders often view established entities more favorably.One of the biggest advantages, though, is the flexibility in negotiating the down payment.