AND. ..if property also needs some rehab- new roof, some unit cosmetic repairs?  

Due to that small forest type of tress growing in that area including poison ivy plants (I spent lot of money few months back in clearing that area from all the those poison ivy plants and forest of big old trees grown over the years touching the roof and leaning towards building).

I only have student loan debtI have a full-time remote jobI have no prior experience in real estate investingMy credit score is high 700'sHere are the details about the property in Zenda,WI:Asking price: $235KIt’s being sold by out-of-state heirsIt needs at least $50K in repairs and updatesThe neighboring house recently sold for $235K (though I don’t have details on its condition before the sale)A family friend who owns a construction company assessed the property and noted the following:Replacement Needed: Furnace, Water Heater, Water Softener, Floor (concrete replacement needed due to unevenness), Roof, GuttersUpdates Needed: 1.5 BathroomsConcerns: Black mold and water leak marks upstairsRemodel Suggestion: The staircase is very steep and narrow; recommended to relocate and extend it into the living spaceAdditional Work: The property slopes downward, allowing rain to flow into the house.

There are critical items such as -Plumbing, HVAC, electrical items, roof repairs, appliance repairs- that you want extremely competent professionals to handle to ensure that you the PM and owner avoid liability and to ensure you aren't shelling money out again for the same issue because you were being cheap the first time.  

Every item from a roof to a dryer has a depreciation schedule that is fairly standard.One income property is really easy to track if you associate it with one bank account. 

I ended up replacing a tar roof on front because it looked too shabby after the full rehab.

After swallowing some lumps thanks to one thread I posted back in April, I should (crossed fingers, no blown furnaces or sheard off roofs) be in a good position next year to reinvest.This is hopefully not a beat the dead horse, "where is the best cash flow in X" post, more of a strategy question for anyone who knows the market in CT.Here is what my limited knowledge/intuition tells me: Waterbury, Bridgeport, parts of Hartford cash flow best because of the inherent risk, lower fairfield county cash flows worst (today) because of NYC effect on price/rent, and there is an in-between SOMEWHERE.I think that somewhere is in the central part of the state between route 8 and 91 north of new haven, east of waterbury.

On another occasion I had them inspect the property after purchase and they informed me that due to the condition of the roof they were raising my deductible on any roof damage to $5K instead of the $2.5K for the rest of the property until I installed a new roof.   

You need a place to live, so find something that provides a roof over your head and the potential for a return.I know a guy that buys fixer-uppers, lives in them for a couple years, renovates along the way, then sells for a profit.

They are willing to sell, but it would need to be at a good price because it needs things that my side already had done (roof update, windows).