When in Due Diligence have a thorough inspection and get estimates for any work that is needed now and potentially in the next 3-5 years. don't forget about the tax benefits to doing the work upfront.

A lot of newer investors hear older podcasts when people where buying brrrrs, making money on the cash out refi and then cash flow.

@Jeffrey Mair I would keep your rentals forever, especially that they are cash flowing. 

If your property management company is good and has built an internal maintenance team which has set rates and had strong relationship relationships with licensed contractor which should keep costs in control, you should never need to shop contractors on your own I wouldn't think.So in short, our policy is give us your preferred contractors upfront if you have them, but then we work all tickets to resolution including dispatch, and payment of invoices.This is of course for operational expenses.  

Assume you have cash currently earning 4.6% in high yield savings.

However, the studio unit was only rented for $800, which is affecting the overall cash flow.

Eventually, I’d like to start using the cash flow to pay myself and work toward replacing my day job income.

For instance, mismatched names, employment details, or salary figures should warrant further scrutiny.Urgency to Move In: Applicants who are unusually pushy about quick move-in dates may be attempting to bypass thorough checks.Reluctance to Provide References: Hesitation or refusal to provide contactable references from previous landlords or employers is a cause for concern.Cash Offers for Faster Move-In: Proposals to pay a significant amount up front, especially in cash, to expedite the moving process can sometimes indicate an attempt to avoid scrutiny.Unverifiable Identity: Difficulty in verifying the applicant’s identity through standard identification documents can indicate potential fraud.Tips to Mitigate Rental Application Fraud:Enhance Verification Processes: Implement stringent verification processes for employment, previous rental history, and identity.

5) If approved, how much will they want upfront, when can they start and what's their expected completion date?

You have to be up front about how the property is being used.Also, remember that umbrella insurance will not do anything for you if the underlying property or vehicle is not insured correctly.