I actually remember my local lender mentioning that it is very difficult to find a lender if any.

Will it be difficult to qualify for another mortgage if my income only increases roughly ~5%?

I personally don't invest in any cities or towns that have a population <10,000 since I find them pretty illiquid (i.e. hard to sell etc).With regards to ADUs being difficult to be permitted, I think that's definitely going to have an upward pressure on housing and rental prices.

@Jermey Hnederson there’s a bit of a shortage at the moment, so finding renters shouldn’t be terribly difficult.

I know that the logo and company name are not necessarily the most important things to figure out, but I certainly don't want to regret our choice years from now when it is difficult to change.

If you stay on the weekends because you are away Mon - Fri, there shouldn't be an issue.Please note, depending on the location, property type, and seller's situation (i.e. their motivation & desired closing date) 203K loans can be difficult to get accepted. 

Is the HOA very difficult.   

Thank you @Mike D'Arrigo, this was a difficult decision on my end but I ended up taking a position with a mortgage banker.

It shouldn't be too difficult - especially after you go through these two videos. 

@Harvey Roberts welcome to the BP community, when it comes to borrowing capital with most traditional lenders, especially when it gets to the lower amounts will be difficult.