Each person has different learning abilities and drive. 1) If your current job pays well you may be able to learn on your own or pay someone (like a coach) to educate you while on the job. 2) On the other token if you need a push, being a property manager or a commercial broker or a lender, may push you further along in learning indirectly if your drive is not that strong. 

4 Unit Building (one floor/ranch style) - located in Chicago suburbs.

I’m now in need of a solid lease agreement as I’m about to start taking applications for tenants.I’ve found a few that look solid but I’m not sure what to trust that I find online and I want to make sure the lease is as strong as possible.Any advice or help or available and reliable templates would be greatly appreciated Thank you!

-Fenced in yard per unit, roof 5 years old, new water heaters within a few yearsFHA 3.5% down (3% of that coming from sales commission)Rents: Local rents vary from $900-$1200Mortgage: $2050I understand this deal will not produce that much cash flow in the short run (Once I convert more equity in the unit I can drop PMI to increase cash flow) Remember, this is my fist deal with little to no money in which doesn't produce a strong cash flow standpoint.

If so, I would very strongly consider the merit of taking on $300k in debt in order to achieve this level of earning potential and perhaps explore cheaper ways of attaining this education.Rather than thinking about how you can mitigate a poor financial decision through real estate, I respectfully suggest that perhaps it's better to not make the poor financial decision in the first place.  

My investment style is fairly conservative (multiple buy/hold rentals) balanced with low-cost index ETFs in our 401ks and brokerage account.

Based on my strategy (that I call Relationship Wholesaling), when you're building a strong relationship with the Seller and really crafting a custom proposal that meets their needs, there's little need to "discuss it" with them (ie talk about it at length or make a big deal of it). 

Land and style of home and the area and privacy How did you find this deal and how did you negotiate it?

Congratulations on weathering the storm of being out of work and then rebounding so strongly. 

You will record the mortgage/refi as Liability.I strongly recommend to do the monthly bank recs, this is something the tax accountants will want at the end of the year.