I ended up giving him some seller concessions (Which I ended up raising the price to make up the difference), he bought with a conventional loan, and overall was a smooth transaction.

I've found that targeting single family cosmetic renovations (anything in front of walls) makes things as simple and smooth as possible. 

Our financial commitment ensured a smooth and expedited transaction, demonstrating our dedication to providing the necessary resources for successful real estate ventures and maximizing profitability.

Other then having a decent cash buffer as backup for vacancy+ things that will break and having insurance for each property what should i need to do to keep the engine flowing smoothly .

And in the STR game, reviews are pretty much everything.Assuming you have the hot tub up and running smoothly though, I'd also take some time to focus on what cold weather amenities you can offer to guests to entice them to visit during the colder months when ADR's drop and occupancy falls off a cliff. 

Our financial commitment ensured a smooth and expedited transaction, reflecting our dedication to providing necessary resources for successful real estate ventures and maximizing profitability through strategic investments.

Our financial commitment ensured a smooth and expedited transaction, reflecting our dedication to providing necessary resources for successful real estate ventures and maximizing profitability through strategic investments.

What are the typical timelines, and are there any tips for navigating this process more smoothly?

Assure them that this process can lead to a fast and smooth transaction without the usual market hassles.Be honest about the property’s condition and why your offer might be lower than the asking price.

It sometimes isn't as smooth once you are married or have kids if you dont want to have a shared space with family around.