So I’m wondering if anyone has experience with other property investment friendly insurance companies with good rates before I start shopping around. 

House hacking will also give you some personal "property management" experience.

Your first few deals are learning experiences and it’s likely you won’t make the best deal of your life until you have more experience.

If you have had any experience with Viking Capital I would appreciate any feedback on your experience.Thanks

However (as you and I both know from experience :-), even the most savvy Investor/Contr can estimate a rehab and then you get started and oooops - didn't see that coming!

So, I would go ahead and turn the garage into an "out of this world" experience, with arcade games and other game room items!

We had a great experience with the lender we used from a big bank since it was a jumbo loan, very knowledgeable and competitive.

I would think of this problem differently: I might encourage them to explore ADUs... this would give them an additional stream of income and would likely only require a relatively small chunk of money in their savings (relative to the total cost).If they could partner with someone that has experience building and/or flipping (to qualify for the construction loan), then cash them out with a 30-yr DSCR loan (and use that as the builder's profit), then they could rent the property and enjoy the cash-flow.

.: One thing to consider: partnership.You have time, knowledge, and experience, but not enough money.

Whatever you do, don't sell your properties because of your bookkeeping experience!