We started our paperwork with the VA through Navy Federal to get the loan transferred.My husband has been supplementing his teaching (which is PT) with remodeling since February of 2015.

Long story short we just received our second supplemental HOA bill in two years time, this one being around 150$. 

You do recognise you are operating a business and supplementing a tenants rent is not a realistic approach to business.

We are now well capitalized and should be able to acquire multiple properties to build our wealth and provide for the passive income to supplement our retirement. 

You can do what you want but the bigger question is why are you supplement the other tenant to the tune of $300/month.

I am interested in real estate but at this point it's feeling like these apartments would be a whole job to themselves, and not something supplemental. 

He sounds like a good tenant, are you willing to use part of the last month rent to supplement the shortage?

I do, however, like the idea of building some longer term wealth through real estate.Who knows where this journey will take me, but generally speaking, I’d like to build a portfolio of rental homes that can supplement my income and help provide for my family for the long term.More specifically, I’d like to purchase and manage at least 1 property in 2016.

Normally written contracts are strictly construed, but if they are vague or ambiguous then verbal supplements are involved and you have no knowledge of what those are.I do have some words for the advice of @John Thedford ...

When it comes to details around financing, regulation and taxation, much of the information is U.S.A. specific and those of us from elsewhere need to find local information sources to supplement.