Lesson learned.I ran it by the agent and said I'd like some language protecting me in case the roof isn't fixed in a timely manner as it may prevent lender from giving the go ahead.

Im prepared for alternatives should the personal loan prevent me from refi due to credit limitation.  

Only that you must establish your intent to hold for investment.But nothing prevents you from later converting a property held for investment into your primary residence. 

@David Detweiler - it’s likely different state by state, but I know in mass one of the additional “hassles” would be having to install a sprinkler system as part of the fire prevention system.  

Major renovations are planned: new roof, new HVAC, tearing down walls to increase HLA, licensed contractors on the premises, and some earthwork around the house to prevent rainwater drainage going through the house foundation.Thank you in advance!

This prevents purchases at significantly over value.  

I tell myself that just getting to this point and buying my first property is a win itself by overcoming the fear that most have which prevents them from ever taking the plunge into REI.   

Tenant shall use felt pads, rugs or similar scratch prevention materials under all furniture items or other items placed upon any hard surface flooring in the Premises.

According to my contractor, the fix to prevent further damage seem to be simple, seal the gap between the trim and window, clean the gutter, and replace the drywall on those areas if needed.

The limit on one STR permit "per building or property" might be designed to prevent people from buying a 4-plex, for example, and using all the units at STRs.