Even those markets with oversupply are believed to be lacking significant supply for the mid-term and long-term needs.

I've heard Stessa and Buildium for the most part but find it's actually very difficult to use for the average small scale landlord (I have 7 doors)The cost of Buildium I think is way too high for the small scale self managed landlord like myself. 7 units comes to $55/monthAs for Stella, the UI isnt the greatest and probably tailored for more property management companies, and the accounting features are rather lacking for Canadian tax laws.

All of that being said, most property management companies of any size likely have full-time or part-time handymen (for lack of a better word) that that service simple repairs across units for multiple owners.  

My beef isnt with the lenders themselves it’s with the misinformation and the lack of actual information needed to make sure you have the resources to apply. 

Don't care enough.Address the lack of title DD and how to handle insurance if you want to increase success rate.  

I'm lacking a network and relationships with like-minded people.

Areas that have been good 30 or 50 years ago are still good today.One wildcard though.The city of MKE has initiated a projected called GrowMilwaukee, which is based on the majors vision to increase population (for fiscal reasons, more people per square mile) and they have identified the lack of midrise mixed use districts - they call it the "missing middle".

However your situations biggest risk is the lack of appreciation. 

However, one thing that did stick out to me was the lack of accounting for Capital Expenditures.

Plus his company has 3.9/5 on TrustPilot, with some of the negative reviews lacking substance.Sean himself showed enthusiasm and patience and it was clear that he's an experienced teacher.