Ideally you should ask what you want long term...If you think the tenant can meet your needs as a landlord while you meet your responsibilities to them then solve today's problem and set clear expectations along with regular follow ups going forward..

Since i'm just starting out i'd ideally like to start with a small investment (just to get my feet wet) and then with a little experience under my belt aim for larger projects. 

That is when we found a problem and what gave me a brain annuerism and a stroke just 2 days before my scheduled preventive surgery from a specialist.I am going to try to leave you out from my problems and concentrate on yours.  

(his degree is Aerospace Engineering) Since he'll need to go the FHA route for his loan to get a low down payment, we're looking for some remote leads on investor friendly lenders and local real estate agents that can help us locate an ideal property for him.  

Whenever I deal with this, so long as the color works either way, I go with whatever the odd man out is.

To keep the space profitable we think designating a space to storage units or opening a restaurant/bar in one of the buildings may be ideal for monthly income.At this time we are contacting local organizations to see if they would be interested in having their events at this facility.

I would ideally like to buy the property, fix up the house then convert the he double garage into either a studio or even a 2 bed and then rent out the house.

Ideally, you will learn the markets you want to focus on, and you will be able to do a rough estimate on whether a place is worth looking at further in under a couple of minutes, and get to whether you want to look at it with an agent in under 5-10 minutes.

In my opinion It's not ideal for rental.. at least here in the US (I noticed you are in Canada... not sure how it works there)Here you have to pay property taxes and insurance... you obviously need to pay for maintenance as well as property management (even if you manage yourself consider that your time = money)... you also need to take into consideration initial vacancy and the fact that sometimes it take couple of tenant's before you get a good one that stays very long termHere once I take all my costs out I tend to make approx 30% of my rent in the first year50% in year two and three 60% afterwards If rent is $1200, it would me bring net $400 avg first 12 months ($4800 first year), $600/mo second year, $700/mo afterwards... probably a hair more if I include a rent increaseYour interest payment after the first year is going to be approx $700/mo... which means you are barely making it.

Sadly, because of all the regulations and scumbag attorneys it's best to let your servicer do it.The ideal scenario would be if you're big enough and can hire your own in-house team and train them to follow FDCPA and CFPB.