The age of the housing stock coupled with the inexperience of a student tenant might make it difficult to keep up with maintenance without a strong property manager.

I have onsite management, but I manage reservations and communications remotely (and I have a full time job, so I really need the software to keep me organized, not the other way around, haha!).  

We have started including disclaimers to property owners when dealing with water penetration especially on interior walls that can come in from the roof, the siding, windows, doors, etc.Generally if you're not happy with your PM you should trust your gut and try out someone else, but also keep in mind 2023 and 2024 to date have been the most difficult leasing years in the last 10 years nationally and especially in Philadelphia.

I plan to self-manage it, should be able to easily demonstrate 100 hours and no one works more than me on it, and keep the stays under 7 days.

Fine if you are doing one or two but when you have 10 going its hard to keep up.

While I'm actively exploring various avenues to improve our financial situation, I keep running into dead ends.

Wholesaler looking for their own deals and keeping the best.

This is why most double closings are performed illegally, not because the double close portion is illegal, but wholesalers tend to circumvent licensing requirements to make a buck.Just as there are legal ways to drive and operate a vehicle, there are illegal ways to do the same. 

Rather most sellers don't keep good or any books so they don't know what their expenses are and most buyers of these units don't understand or know how to evaluate based on cap rates.

Using antifreeze instead of water keeps it from smelling if you aren't able to check it every day.