She's been renting it for $2,800/month and the condo has a $600 monthly HOA.I want to offer her $350,000 for the condo (its a fair price for it), 5% down payment ($17,500) and pay her monthly $2,000 for 3 years, after which I would refinance and pay her out.

If he is making monthly payments of ($1,394.49x12)/135k= 12.39% cap rate.

But, most  municipalities will settle these for 5-10% from someone who comes in and fixes the underlying issue.Some research and leg work may lead to this being a non issue (insurance company pays the claim/contractor) or maybe not…but worth putting some work into it.

In Florida, the answer depends on whether the rent is being held as advanced rent for each month or if the payment is for the entire year.

Appfolio is pretty robust, it allows you to track subsidized housing payments; the maintenance and accounting system is all tied neatly together.

Also, what are some good resources to compare newer tech for potential equipment upgrades etc to get the equipment onsite converted more to cashless payment systems?  

I am not sure how you plan to handle rent collections but if you think there may be times that a tenant will need to pay via some non online option then having a bank in the area of the property can be good.

Call the non-emergency number for the local police station and ask them who to contact to get information. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620, many blemishes, but should have no evictions in last 2 years.

Best way to use it to avoid getting hit with the higher payment would be to set the payment up on a Bi-weekly and use the cash as a 'All cash" purchase.When you use "All Cash" on a purchase you can then get a "Delayed Financing loan up to 80% LTV to get the majority of your capital investment back into liquid reserves even on a investment.