In the short term, I aim to replace my monthly income from my current entry-level job, I dont make a ton of money so this shouldn't be too difficult.

I would like to get something setup to help connect all of the different teams you would need to do a full job from finance to maintenance and everything in between. 

There are new neighborhoods & jobs popping up rapidly in the area and expanding further South into Tate County, MS & Southeast into Marshall County, MS.

Has he  been working remotely for his job in Canada? 

Appraisers do not like being told how to do their job!

However, this is a difficult qualification to meet, especially if you have a full-time job outside of real estate.Don’t worry if you aren’t able to qualify for REPS status, because there is another strategy that is referred to as a “loophole”, which is the STR strategy.Per Section 1.469-1T(e)(3)(ii)(A): there are six exceptions where your rental property income is not automatically considered to be “rental activity” and thus may unlock the door for being able to offset these losses against your active income.The average customer use is seven days or less.The average customer use is 30 days or less and significant personal services were provided (for example, daily housekeeping).Extraordinary personal services are provided, regardless of the duration of customer use.The rental is incidental to a non-rental activity.The property is available during defined business hours for non-exclusive use by various customers.The property is used in an activity conducted by an S Corporation, partnership or joint venture in which the taxpayer holds an interest.If your property qualifies by meeting one of the exceptions above, the next step is to demonstrate material participation in the rental activity.

I finally got a professional in to finish the work, but based on schedule slip on my end and the cost of the handiman I ate into the margin I got on the purchase. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

I have seen too much of how bad of jobs contracts can do when left to their own devices.  

Do you include scheduled inspections in your lease?