Trying to run a successful PMC is difficult but trying to run multiple companies - VR, Annual, cleaning, and landscaping is probably going to give you an aneurism.

I have noticed that it has become a little more difficult to Find FSBO's and such on these popular FREE sites, however,a) Is anyone still using them?

FinancingADUs are rather difficult to finance historically, but that is getting somewhat easier.

First is that its difficult to quantify the amount to charge like you indicated.

If you find it difficult to rent then you can always explore the credit option.

Duplexes are cheaper to rent and expenses are becoming difficult for the average tenant.  

I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

Insurance rates and interest rates are making it really difficult to find deals that work.

This is a difficult sale... finding someone to invest is a difficult sale but asking them to invest for decades is going to be an almost insurmountable sale. 

After some investments in amenities (primarily hot tubs), our last 3 months have averaged 12k/m.This property is owned outright, and due to the size of the property, the small square footage of the units, and the lack of comps in the area we have found it difficult to lock down any refinancing.