First, a lot of people with Section 8 vouchers end up staying in the same neighborhood because it’s where they feel comfortable, where their family is, or just because they know the area.

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

Ensure the STR’s projected income comfortably covers new debt, even with conservative occupancy rates, and maintain reserves for market changes or vacancies.

If house hacking is not an option, you can try out-of-state investing and check markets you are comfortable exploring. 

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. 

I want to provide a safe, structured living environment for individuals transitioning out of recovery or other challenging situations.I’m new to this process and was hoping for advice on the following:How to navigate zoning laws and permits in Montgomery for this type of setup.Licensing requirements for sober living or group homes.Strategies for finding residents or partnering with local organizations.Financial and operational tips for managing this type of property.I’ve heard zoning can be tricky and want to ensure I comply with all legal and safety requirements.

i agree with you on the tough environment there for purchasing / house hacking but I wouldn't give up on that regardless of what else you look into. house hacking = owning real estatewildly successful arbitrage = not owning any real estatecan you look in Frederick MD or Fredericksburg or Ashburn or an exurb? 

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.