But you if are not understanding too many things, and it is keeping you reserved from making the move how then do you approach this? 

I was never a fan of it, but now that a lot of great points have been brought up, I will stick to my guns and continue to make sure potential tenants are able to verify their income. 

Hello BP,  I am 22 i just brought my first home last year at this time, I am ready too start investing in real estate.

So, approach a local bank about a "cash out" (commercial) refi loan against the property to do "renovations and upgrades". 

Your approach of finding an experienced agent and lender is critical, because the agent will have to build in that expectation up front. 

You forgot to mention the small detail that included with that scenario, there is the requirement for the loan to be brought current.

Alas no.  2 units can be brought online for this season, but the other 2 need more major work (reroof and  layout issues).You mentioned paying the agents commission...how much is that?

No matter how I try to approach it with her, it ends up getting pushed to the side because the idea of 'playing with our money like that' stresses her out. 

Some of the issues brought to our attention by current tenant would need to be addressed by the seller before acquisition.There is a potential piping issue or cracked pipe somewhere as the tenant complained about some water level problems.  

He was approachable, professional and on further research has had a very lucrative career to date.