Numbers look good on paper, but generally low rents, a lot of section 8, low quality tenants, etc. 

A 988sf roof w/ a 6/12 pitch is only 1,105 square feet of roofing w/ a 10% material waste that's ~12 squares of shingles.Roof Quantity CalculationOakridge roofing shingles are $140/sq at Lowes.12 squares*$140/square = $1,680 in shingle materials + a few hundred dollars of underlayment and flashings, so there shouldn't be more than $2,000 in materials.So in other words your Contractor has quoted you $9,000 for labor for a roofing job that will likely take a crew of 3-4 guys one to two days tops. 

I go up slightly (my initial offer bakes this likelihood in) and if the seller counters again I explain why I can't go any higher (all good reasons - winter's coming and the gas bill will not be low, it'll take at least two months to rehab a unit/units and fill vacancies, etc.). 

Comps came back anywhere between $150k-$340k.Current rents are low, property has 2x 3/2 and 1x 2/1.

There is also the chance that you just blow an awesome deal because you low ball too much based on what you have learned on BP without real world experience in your market.Buy your first rental properties in a way that makes financially sense - for high cash flow.

The attractively low price, oversized lot, and tons of concrete improvements made this acquisition a no brainer.

You should look for a steal in the surrounding area (you can draw a map as you search on Zillow) or try the area in the Valley Arts section of orange, its near the campus, the price of the properties are relatively low and theres a midtown direct train there (the highland park station)

If you cannot find a deal in Jacksonville, look an hour south to Orlando...With tourism and hospitality as its main economic drivers and backed by unprecedented population and employment growth, Orlando’s multifamily market is thriving.The metro added almost 47,000 jobs in the 12 months ending in May 2018, keeping Orlando well above the U.S. average.

Nicholas,As an investor myself and an investors real estate agent - I'd say it has gotten harder to find good cash flow if you're looking to do FHA or VA super low down payments.

I suggest you look at local tax rate, insurance carefully, utilities are low if you have to foot the bill.