My question is whether I need to trust my analysis and agent to find a deal and wait for a BRRRR so I can scale quicker, or play it safe and crank out another house hack in May.

Cash offer do carry weight as they can close quicker, don't need appraisals etc, but as an agent that works with buyer and sellers, I've seen it many times where a seller will pick a different offer due to some connection to the buyer (ex military, young married couple just starting etc) They want to know its NOT going to an investor specifically. 

This was my experience.I know it’s a lot to consider but I hope you’re able to find a resolution that you’re content with.

Also sellers who offer buyer broker commissions will probably sell their home quicker and for more money.

So it could take months (or years) before a resolution. 

The more you use this Forum, the quicker you'll find what information to include in your posts.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

The loan process is quicker too.

Take the back rent it will not change your house status.Then tell the tenant they must pay going forward and if they don't be quicker on filing an eviction.

There are no prepayments on these, and the underwriting process is a lot quicker, but you will be paying a higher rate than a DSCR loan.