It doesn't feel successful, I know, emotional investing is not the way to do it right, so I will concentrate on the loans with higher rates.As far as the loan that affects my debt to income ratio the most, that is definitely the 600k loan I cosigned. 

The mortgage bank sales middle management people are rapidly becoming obsolete (they are the #1 reason you might find it hard to compete on rate with the jenky internet lenders).

You should not be essentially required to have internet/a smartphone to rent from somewhere, even though the vast majority of the population does.

And it’s in the internet.

Some are going to be popular and most won't, that's just the internet. 

South Florida has the highest concentrations of vacation homes in the US.

How much of the $226,000 capital gain ($326,00 minus $100,000) was due to the inflation over that years since 1994.According to an internet search, between 1994 and 2019 there has been 73.1% inflation, therefore of the $226,000 capital gain, $165,206 was due to inflation, and leaving $60,794 as "pure" capital gains minus inflation. 

I also was concerned that since their share of utilities/internet etc is included in the payments they send me, that I would pay income taxes on what is going toward those expenses.For context:Mortgage: $1100Cost of mortgage plus utilities: $1500Roommate 1 rent: $450Roommate 2 rent: $400My share: $650 (because I take the master suite)My brother is living with me while he tries to get on his feet in a new city, I don't exactly charge him rent but he gives me $300/month voluntarily out of appreciation, and the plan is for him live here permanently and formally pay rent (a higher amount) once he sells his out-of-state property.

DONT BORROW MONEY ON THE INTERNET!!!!!!!!

Really isn't a big concentration of 3-4 unit properties anywhere in the Cleveland market.