Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

You can sell the customer base, the website, and more as business assets.  

In this case, your monthly payment with 20% down will have a good MARKET rate if your DTI works with a much lower month payment and no mortgage insurance(MI).

Some numbers:Expected 2026 income after raising rents to market value and assuming 7% vacancy: $144k.Expenses: $14k property management, $18k property tax, $10k insurance, $10k utilities, $8k in repairs/maintenance/advertising/admin/etc: Total operating expenses: $60kNOI: $84kBased on 6% cap rate that brings the valuation to only $1.4m, or $1.5m based on 5.5% cap rate.

Anyone have any advise when it comes to liability/insurance if i have a pool at my airbnb? 

This is not a great return, but not terrible.As others noted, there are other risks, like having the property insured at full replacement or purchase price, or if the option is 100% seller financing with no money down or very little, versus 20% traditional down payment, this can start to move it into a better investment.

It's an estimated cash on cash return given current rental rates subtract expenses assuming 7% interest rate, 10% management fee, 5% repairs, 5% capex and other expenses like mortgage, insurance, tax. it's a estimate to tell you what properties to analyze vs ignoreyou can see the are pockets of negative returns as well as pockets of positive return. this is to supplement the data @Devin Conley provided

Some of your requests may fall outside this manager’s standard practices, and customizing services for each client isn’t practical for most PMs.

Anything above that is billed to the customer separately by you.

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.