Depending on what state you're in, you may need a real estate broker's license to start and operate a management company.

For bookkeeping it depends on your portfolio.A portfolio of 1-3 SFR's can likely be a DIY project.For 4+ you may want to consider outsourcing.For tax prep, you'll likely want to have a pro handle it regardless of the portfolio size.

CT is 1-2 hour drive from my location depending on the town and is manageable for one project.

It really all depends on the amount of risk you want to involve yourselves in. 

Best I can tell all in all we about 3X cash on cash over 5 years.infil lots depending on lot we could double our money in 9 to 12 months cash on cash.. so on and so forth.

- Does this answer change/depend based on my current tenant's wishes? 

Pick a screening platform/application that makes sense for you.As for meeting the applicants, I recommend meeting them at the property to show the place to them rather than getting coffee or food with them.

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

But I’m sure that depending on the area that experience will vary.