I am going through the regulations and restrictions in that place (not a closed community but there are some rules).

What I've seen before is the only time rules are enforced are when neighbors get pissed (ie STR neighbors).I would side with caution on this, especially if it is a newer built community where the rules are fresh with people. 

I'm also bringing another investor (Strong) who will take out a loan for the 250 Be careful of the various rules.  

There is plenty of good turnkey properties on the MLS for sale that would cashflow using the 1% rule and you wont have to overpay for them on a "promise".

Apply the 70% rule to determine your maximum allowable offer, then negotiate and get the property under contract, ensuring your agreement includes inspection and financing contingencies.Arrange professional inspections to uncover any unforeseen issues, using these findings to negotiate concessions or confirm your repair budget.

Furnished Finder does make it tricky since you need separate profiles for each room, but platforms like Apartments.com or Airbnb might work better if you're aiming for full-house rentals or structured by-the-room arrangements.If you decide to rent to multiple individuals:Tenant Screening: Screen each tenant thoroughly to ensure they’re reliable and responsible.Clear Communication: Introduce potential tenants to one another Detailed Agreements: Use separate leases for each tenant and specify shared vs. private spaces, utilities, and maintenance responsibilities.House Rules: Create clear, written house rules to prevent misunderstandings.Inventory Tracking: Document everything in the home (furniture, appliances, etc.) to avoid disputes about damage or missing items.Also, market your property with its flexibility in mind—like proximity to hospitals for traveling nurses or universities for graduate students.

However, consider calling the VA’s regional loan center or speaking with a VA-approved lender who can interpret the rules in a more specific scenario tailored for you.

i think selling to other investors would solve some of this, as i believe the same rules do not apply to rentals as to primary residences. 

If she doesn't pay the rent in Jan, start by following your local rules for non-payment of rent (normally a 10 day notice). 

I had a similar off-season challenge and decided to allow pets ( with restrictions and clear house rules) and I gave a 30% discount to try & attract  snowbirds ( I’m in FL) - my calendar filled up for a few  months with a few pet owner bookings and  2 separate 45 night bookings,  did all this on pricelabs & airbnb -best of luck !