While doing the research I have seen most of the properties have all the dates open, which doesn't bode well.

That money has a due date.

Always ask to see the tenant’s voucher before signing or submitting the RFTA packet.The approval and inspection process can take time, and if the unit fails or the paperwork is delayed, the tenant may not be cleared to move in yet.Check the expiration date on the voucher to ensure it’s still valid.

Your tenants can set up automatic drafts for their rent payments, but make sure they do not set them up for the due date, as they will not process.

Just scroll to the bottom of your listing link and you can see 4 places that are quite a bit nicer for under $1500.You are offering small 900sqft with an original kitchen, only ONE bathroom that is dated and has no counter space, an interior that is a mix of finishes and colors, tile ceiling, super basic light fixtures, no garage and a totally overgrown yard - all of that screams total neglect.

As a beginner you should 100% have a good buyers agent who can explain the contract and your contingencies, dates and deadlines, dos and donts etc. for you.

I ended up connecting with a lawyer who has handled other issues for me and she said basically I waited too late in the month to start the eviction process and to sit tight as it seemed the tenant was actually moving out, but if they weren't out by designated day, circle back to start a formal eviction.What actually happened is that the tenant moved out on the date indicated and left some trash but the unit was generally clean and left in good shape.

(Important timing note: Federal tax liens automatically expire 10 years from the date of assessment under IRC §6322. 

I work primarily with investors focused on short-term rental–friendly oceanfront properties, and something interesting has been happening here:Many of my clients are applying a modified BRRRR strategy to dated oceanfront condos — essentially:Buy older, underpriced units in established resorts → Renovate to STR-grade finishes → Rent on Airbnb/VRBO → Refinance after 12–18 months based on new income comps → Repeat with equity pull-out capital.Even though condos can be trickier with financing and HOA dynamics, the math has worked surprisingly well when:The HOA allows STR operations.Renovations target higher ADR and occupancy.The appraisal reflects short-term rental income rather than long-term leases.I’ve noticed this approach works best when you treat each condo almost like a “micro–multifamily” — tracking cash flow, management efficiency, and appreciation just like you would for a small apartment deal.Curious — has anyone else here applied the BRRRR method to condos or coastal properties instead of single-family or multifamily units?

I would love to see our traffic and bookings increase by making the change to flexible, but I think I'm taking too great a risk making our property otherwise unavailable while the guest has the opportunity to cancel so close to the arrival date, which likely will not be booked by last-minute travelers.