I specifically asked him to talk to the underwriters to make sure the STR would lend. 

They had a very specific vision for a dream beach house.

Year of update of the systems (roof, plumbing, electric, heat)4. any pets, pools, tranpolines, or business use at any locationThey will usually need more specifics but this is a good start. 

or the split model where guest pays part of that …Anyone have specific experience on these two issues?

Hi Jacqueline-Great questions and I also help investors as an agent in Michigan.Typically, I work with investors that like a particular area I have written content about and have shared on Facebook real estate investor groups in those areas or posted on my website.Then, I work with them to define their investing goals and specific buyer criteria so we are only looking at properties that fit that.It has not been a problem working with investors after defining their buying criteria because only a few properties will meet that criteria.To your success!

I currently use LawDepot to download my state specific California residential and then save it in PDF format, but then want to e-sign it myself.

There are habitability standards specific to each location that you as the landlord would be responsible for. 

I am looking at multifamily specifically as I doubt numbers would work for single family there ( but would do that as well if it works).

Don't know this specific "mentor" but I would typically advise to steer away from them.

Possibly just one off with this specific lender and I need to try to go to someone else.