Having to order custom windows really pushed back the timeline.

I reached out but the thing is that they have a customer service type number and you can't get to an actual assessor.

Yes, as other people have mentioned - DSCR Lenders have prorprietary guidelines and generally offer more customized and shorter seasoning periods.  

I borrow at sub 8% and lend at 12% so I know.  

if we choose sub contractors for each work and we manage all the work independantly then need to take insurance is that correct ? 

Since that time, it is Top 1% in the sub-market, occ% is just about 75%, and avg ANR >$600/nt.

Their customer service is second to none and they've got more education and networking opportunities than any other company. 

Also, you don’t need  $360k if the loan gets called; with a principal loan balance of $240k it would be more like $250k.Whether you do a wrap, sub to, or lease option when dealing with a owner occupant / consumer there are many legal “traps” to navigate because of consumer protection laws at a state level, and CFPB and Dodd Frank at the Federal level.  

I will send you a private message with my guy Francisco, a super sharp HVAC sub in Chicago.

I don't know the details of your lease - rents, length of lease, triple net, commission amount - but if it makes financial sense and makes the customer happy then absolutely pay for it.