-We have 3 years, or until we buy another house, for one of them to be considered a 'rental property' and subject to those capital gains.

If it's over a year, you'll  be subject to long term capital gains at rates up to 20%.

With the increasing number of lawsuits and penalties for TCPA violations, I'd like to cover my backside and remain compliant.How do you scrub your lists to ensure you’re not contacting people on the Do Not Call list?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

However I am wondering what I need to have in addition to cover repairs and others things that I may not be considering.Any advice and recommendations would be much appreciated!

In analysis of subject propert the cap rate for 103 property in this area is 5.4%.

However, before you do so you should ensure that your revenue from rental income covers ALL your property expenses in the townhome, including mortgage, taxes, insurance, maintenance/repairs, vacancy, property management, etc...

Would it be reasonable or unreasonable to tell our tenants they need to cover the cost of the repair, several months after we had told them this guy would repair it for free?

If it's the difference between $1800 and $2200 but you have to cover utilities too, not worth it. 

My plan is to funnel the rental incomes from all three properties, along with my W2 income, back into the HELOC while covering all expenses from it as well.