Are there any lenders that anyone is aware of that would feel comfortable lending about 325k for a 5 unit property?

There are so many rentals in the area, probably on shared wells, so those people have either decided the STR use is okay or they are comfortable risking it.My intuition is that any actual disagreement over water usage could be handled with the other owner; but the risk would be if the other owner just doesn't like the STR and wants to use the well agreement as a reason to demand it be shut down.Any advice would be greatly appreciated!

It all comes down to picking the right areas that work well with your personality and attract the type of clientele you feel comfortable working with. 

And unless you have very deep pockets, you can't afford to be that much off....So as has been said....hire a very experienced General Contractor and have them give you a budget number based on your SOW, (plus they will find other things that need to be done that you will not have seen).On your succeeding projects, you do a budget yourseld first, then hire the GC and compare numbers.Then, eventually you will be comfortable going all solo...but it takes time.

Once you’re comfortable, focus on creating content that reflects your business’s unique personality and values.If editing and creating thumbnails feels like too much, hiring someone on platforms like Fiverr or Upwork can save you time.

In short, if you’re comfortable relocating one of the sides to move in, and comfortable to live in the place, than just do it.

It all comes down to your comfort with risk and how fast you want to grow.

This summer, I’m heading to Florida and found a new resort that looks amazing for a relaxing getaway.

You should screen everyone the same, but still, it's a bit of a comfort knowing FF is mostly all working professionals.

I'd also recommend joining a local Indianapolis based REIA asap. the REIA will provide a group of investors who could get you some contractor recommends if you decide to GC the prop yourself.You said it "needs a little work done" but budgeted $50k so those two things kind of contradict unless the home is a larger home...just curious, what's "a little work", if you haven't had an inspection yet and don't feel comfortable evaluating the costs on your own?