If you include the costs to build in a purchase of the primary structure, then you can typically roll that into the final loan product.

During the slow season, do you personally focus on getting more rentals, focus more on family/personal life, or do you do something else?

Quote from @Sara Valentine: I have rented my personal home as a fully furnished/lots of amenities 3 month rental jan, feb, and march the past 3 years.

I personally use Hostfully and their support team is great!

I actually had a fire MYSELF, yes personally. 

He is very good about deductions on tax returns so his income looks negligible and of course banks wont talk to him about loans.

What appears to be great "curb appeal" to one person might be overwhelming to another. 

I am hoping to make connections to learn more about this market, which neighborhoods to focus on, as well as learn some pro tips as I begin my investing journey.To note, I have begun the loan pre-approval process and have a dedicated agent that is eager to find me a great property. 

How does the transaction work between me personally and my holding company LLC?

I suspect the person who originally turned it into a fiveplex only applied for permits to make a fourplex and then did the 5th unit fly by night (perhaps at a later date) in order so the property would still be considered residential and allow for better financing possibilities.