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

I generally rule out most single family homes as viable rentals, as prices are pretty high relative to rents, so aside from some downtown neighborhoods, typically you do not find large areas of single family rental neighborhoods (a median sale price on a 3 bed, 2 bath home so far this year in Dane County on MLS sales data is at $430k). 

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.

They actually failed to pay taxes in 1983 as well according to the follow up article below. 2 years later in 2017 the County reversed the sale voting 7-4 against “these out of town speculators trying to make a big payday” and for the fine people of their district. https://www.sfgate.com/politics/article/SF-supervisors-to-vo... well if the county sups could unravel it then the rules have certainly changed from my days of buying CA tax sales in the 60 70s and 80s.. once they went to bid 4 assets and away from the live auction the screaming deals were done.

It still is very possible to find properties that meet the 1% rule without much difficulty; but it’s also tougher now to find a mortgage for anything valued under $100k – regardless of condition or P&L.To me, the shenanigans Code Enforcement continues to play on a new owner after a sale plus the recent increase on the annual rental registration fee really discourages buying more in the City.

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.

A more typical rule of thumb is to budget 10%–15% of gross rental income for maintenance and repairs over the long term, depending on the property’s age, class, and location.

Here’s some perspective:1% Rule: Meeting the 1% rule is a good sign, especially with many markets struggling to hit this benchmark.Cash-on-Cash (COC) Return: 8.73% is decent, especially with today’s higher interest rates.

For tax purposes, it’s about whether you pass the 750-hour rule, the 50% rule, and meet the material participation requirements.

The reality is it's a huge focus for me with my fourth and likely final happening earlier this year.