(Save all applications along with notes if necessary surrounding each round of applications)

Yes, insurance companies have specific panel questions on their applications for older buildings. 

When going with a larger company like that the quality of your experience will be limited to the quality of the sales rep assigned to your case and won't have anything to do with the quality of the company as a whole. 

I now have to re-advertise the place and go through applications again and it could take a couple of months to get another tenant in there. 

Traditionally Non-QM doesn't have any limits on the numbers of properties financed?

I am trying to decide between using the 203k loan which I know limits my options or if I should use a combination of private money and a HELOC that I am applying for as we speak.

As far as financing, I feel l'm kind of limited since I'm not eligible for FHA or other owner-occupied options. 

Subletting is allowed by the tenants lease, but tenant never went through property steps with landlord to bring in a roommate (application, approval, etc).  

Hello Bigger Pockets Community, I would like to begin investing as I have been interested for years with limited resources to get started.

Novogradac is always a good consulting resource if looking for a contact to guide you thru application and allocation.