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. 

Property needed everything, replaced roof, installed central hvac, refinished hardwoods, painting throughout, and more.

However, the more hands-on you are and the better you know the property and avg vacancy rates the more you can adjust these numbers.For example, in terms of expense, if I'm looking at a townhouse where the HOA covers the roof, siding, landscaping and I know the HVAC and appliances are pretty new I'm assigning a lot lower expense to repairs & cap-x.

If it were me, once I had my financing strategies in order, I'd look for a realtor that is also a proven investor themselves and understands numbers and all financing options....people I recommend in our market are Marcus Auerbach, Homestead Realty, Premier Point Realty & Modern Milwaukey Realty all brokers who are also successful local investors.....as it pertains to real estate investing, having a realtor that is skilled in investing is the same as choosing an accountant because if you're going to be involved in real estate, you definitely should have an accountant who specializes in real estate investing and not just landlord investing--ALL aspects of investing from rentals, flipping, self directed/SoloK, structuring etc---they should love real estate as much as you:) I was just involved in a deal on a Cudahy duplex house hack where the investor used FHA financing from Lower.com and I was quite impressed with them.

But deferred maintenance like roof, parking lot, and other big issues should be taken into account.You should probably connect with a tax strategist because it might benefit your business overall to paying higher rent, get higher debt on the property, and have significant writeoffs through a cost segregation study.

Painting, carpet, and light fixtures are small cost items compared to termites, roof, plumbing, wood rot, electrical, HVAC, and foundation issues.