We'd eventually like to move into buy and hold properties but thought we would be more comfortable flipping a house or 2 first.

I am also debating trading up into multi-family once I am comfortable enough.

“Your Honor, he told me I could stay for free as long as I paid the utilities”.

I hate it in my personal house, but it stays for now.

The provision of emotional support, well-being, comfort, or companionship do not constitute work or tasks, so these animals are not considered service animals.

He says he is very interested and knows my other tenant who is still staying in my other unit (unit A).Somehow I am bit worried renting to their “circle of friends”.

After you've acquired 'enough' you can then consider the snowball method if you'd like... or just be patient and let the renters do their job.Option A only becomes relevant when you're no longer in a growth phase or unless it's a personal comfort issue. 

This may be the only chance I have to jump into a 5 unit for the next 10 years.I currently have just SFH's and even though I've done a bit of reading on apartments I'm not even close to comfortable with figuring out what a building is worth, so I have that risk. 

I know it's hard to find an agent who is comfortable working with investor properties.

FWIW, I found that having a partner allowed me to get out of my comfort zone a bit and work through "paralysis by analysis" and take action.