I will have more failures than successes on this project. 

If the tenant does not keep the basement clean to an extent that it might be attract mice.The contract does not have any explicit language stating "Failure to do so will results in penalties or such and such...".I dislike sending multiple reminders.

Don't think that one particular out of state market will shoot you to success or abject failure.

There are 1920-1930 vintage properties  with recently updated mechanicals and a new roof and there are the same vintage properties that need work. 

Without complete financials up to that point, extra work (and headache) will be required to get everything straight after years of failure to keep complete financials.There also might be an asset protection wrinkle by not maintaining complete books for an LLC, but I won't comment on that as I'm not an attorney.

I’m just afraid of setting up myself for failure since it’s my first rental property.

Phase #1 - Recovery  - characterized by high vacancy rates and no new construction- rent, during this phase, is flat or declining- owners offer rent concessions to avoid their property occupancy rate from  decliningPhase #2 - Expansions- characterized by declining vacancy and the start of new construction- occupancy improves, concessions are not being offered, and rental rates being to growPhase #3 - Hyper Supply - characterized by new construction and vacancy rates beginning to rise - rental rates begin to grow at a slow rate- rent concession are being offerred due to the new construction in the area [in the hope of retaining current renters]Phase #4 - Recession - characterized by the completion of construction and a decline in occupancy rates - concessions are abundant to avoid high move-out rates Here are some foundational truths about optimizing your investments:#1 sow seeds of success in the down times - "The season of failure is the best time for sowing seeds of success."

So, now that you got your losses and failures done - and congratulations by the way because I can't think it could go any more wrong - now you can start over.So yes, get those properties sold and do this right this time.

It is mechanically sound with new roof and siding in 2017.

The Philadelphia Housing Authority (PHA) recently acquired a 360 unit 12 story multi-family building for $24M and  a local news outlet  reported on the building.  Through PHA sources, the article indicates the renovat...