Since I'm looking out of state for these investment properties, in places where I typically don't have familiarity or 'boots on the ground', I'm struggling to find the right process to vet these various providers (General Contractors, Lenders, Property Mangers, etc).

Typically the condo fees on condos will knock out your cash flow.

If anyone knows the Virginia market, this property is located in Petersburg, VA in case that influences your feedback.I have negotiated subject to and owner financing to purchase the deal using the following structure: I will pay $8k in cash I will take over the existing $59k mortgage payments (28 years left) of $506.70/mo PITI paymentsThe owner will wrap the remaining $8k into a second 15 year mortgage of principal only payments of $44.44/moTotal monthly payment $550/moThe Deed of Trust will transfer to me at closingI will sell the property via Owner Financing to a tenant buyer using the following structure: Purchase price $85kPay $10k downI will finance the remaining $75k for 10 years at 10% interestMonthly payments of $1000/moBuyer may cash out anytime after the first 5 yearsTenant buyer covers repair costsDeed of Trust transfers when tenant buyer cashes property outBasically this strategy is a way to get all my money invested out of the property and avoid typical rental property expenses to keep all of the cashflow.

What steps do you guys typically take when analyzing an areas rent potential?

Some do but they typically offer lower LTV's when compared with HELOC's on primary residences. 

 @Moises Suazo,If the house needs work then we would buy with a rent to own and typically sell it on through our work for equity program to a contractor. 

Taxes & Insurance are typically around $600 a year for each here with these properties.

Most attorneys will settle a transaction as part of their fee, but even if they charge a few hundred extra, the title company charges just as much typically for settling, so you're just moving that fee to another part of your settlement statement.

It seems like it would be a daunting task to find and contact every individual commercial brokerage.

My experience with meetings that are run by an agenda pitching person, or team, has typically been a waste of time.