So based on my brief description of my background, would you all say I'm ready to take the risk on my own, or would it still be highly advised to work directly with someone who is currently successful at doing so?

This may not be a big deal to a rural based farming family, but it can be a big deal for a commuting family.  

Based on your original paragraph you need to raise rent and/or remodel so you can raise rents.

If you're in the short game trying to capitalize on market fluctuations or appreciation, the risk is that you might buy at the top of the market and get stuck overpaying with few exit options.if you're playing the (really) long game, then it matters much less.

I'd be able to cover the loan payment based on what I'm typically offered for a housing allowance.

I've never had an issue splitting the utilities based on RUBS and getting paid after billing them quarterly.

You get paid based on how the contract you use say you get paid.  

Roman Cervantes Jr Your decision should be based on your incoming cash, current cash, and cash goals.

Assessors determine your property taxes.Your appraisal is based on similar styled and sized homes sold within the last 3-6 months (12 months max) within a 1/2 mile to 1 mile radius, and with similar amenities and lot size.

Touch base with a real estate agent and have her do comps for the house sight unseen.