You have less maintenance as the $140/month HOA will cover roof, exterior maintenance, CAM, etc.

Still have to account for roof, appliances, hvac, hot water heaters, etc.

It will be a factor if other aspects are not adhered to but if it is the only one not very likely.

Furnace, Ac, and roof are all in good shape for now.  

I am wanting to start getting into the rental property aspect of investing.

If the property is in good repair they can sell the property much easier and so they tend to shy away from a property that needs a new roof or is what they deem a dump.Regarding if I can pay them every single month, they do consider any vacancies and will likely demand I have the money in my bank account to reflect X number of months of unpaid rent due to a vacancy, especially if I need to make repairs to the property prior to being able to rent it out. 

On top of all that, we had a flat roof that was newer and warrantied, but we still fought leaks.

If you don't have credibility, or haven't done many deals, you lean more on the trust aspect.

In this case, The parking lot needs to be done, the exterior is super tired and do the roof...

This mainly pertains to your roof - IF you have an RCV policy - do not switch anywhere else -- that is a good price and a good policy -- if it's ACV you can shop around -- try Shelter too -- I worked for them - all my coworkers were fair -- I just wont get a policy there -- something to do with not ******** where you used to eat and if I had a claim it'd be weird to deal with my former co-workers -- would rather deal with people I dont know.