Flipping on a land lease with high HOA fees = challenges that could impact profitability. $700/month HOA fee may deter buyers, elongating your resale timeline, and could push your ARV closer to the lower end of your range.

If I had to pay my cleaners on top of the loss income it would impact even more as my cleaning fees range from $100 to $400 depending on the property.  

@Kaleb JohnsonRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

This includes contacting the applicant’s employer and speaking with their supervisor to confirm job stability, income, and reliability​. if the person has not been employed at their place of employment they would require a guarantorCredit Score and Debts: Applicants need a minimum credit score of 620, and while we review debts, medical debts are generally not disqualifying unless they impact overall financial health.Criminal History: We do review criminal history to ensure safety and security for our tenants, while remaining mindful of state and federal guidelines.Rental History: Positive references from past landlords, with no evictions or significant lease violations in the past five years, are essential. and we can see into the court system if they have an eviction judgement.Release of Information: We include a release form allowing us to verify employment and rental history directly, which helps us get a clearer picture of an applicant’s background.This process has worked well so far, but I’m always open to improving.

and I gotta tell you it's really fun to get to see the impact of my legacy gifts while I'm still around to watch my children prosper.  

And how much of this (taxes, regulations) is a reaction to investors setting up STRs anywhere and everywhere without any consideration to the neighborhood they are doing it in and the impact on that neighborhood.

Either would be a great option; I'd probably choose Roseville because it's more established, but the City of Elk Grove deserves a lot of credit for its impactful growth programs, so it wouldn't be a bad option. 

We offered our impacted tenants a hotel room while we were awaiting repairs, but both tenants decided it was easier to stay put. 

I love your idea, I think it’s a great way to make an impact.

You could probably afford $20,000 without much impact on your budget.