In our area, I would go with the 4/2 vs a 5/1. 5/1 is not conducive to modern buyers.

But, if you really want to learn and experience real estate INVESTING as an employee, you would need to find a job with a company, such as a REIT, real estate syndicator, real estate division of a endowment or private office, etc.

More of a buck shot approach.Find a reputable, experienced (loans and investing) loan officer that does hard money.

The folks planted behind those loan officer desks remember it, and the underwriters are all a bit jittery.

The house is 1100 square feet as it stands but the attic is large enough to be converted to living space which would add 200 square feet to “living space” it also a business zoned lot and also has a small building near the road that was built in the 50s and was used as an accountants office.

Any lender should be able to use 75% of the projected income from the other 3 units. keep inmind that there are rate adjustments for purchasing more then one unit, so when you get pre-approved make sure that you mention to your loan officer that you are looking to purchase 4 units. 

We added value by way of a thorough update and modernization of the property.

Have you gone through that with a loan officer?  

The county accessors office website provides detailed info on every property, including taxes.

Lately, there has been a general increase in the adaptive reuse and redevelopment of hospitality and office space into multifamily projects.