So far the condo investment has been pretty hands off as the HOA handles most things

Hey Chris, a few thoughts here.Considering that office is not attached to the house, I wouldn’t add any footage to the total home square footage; however, you could advertise that office space and amount of footage and amenities in your remarks.If you’re a Realtor or are using one for the sale, your local MLS may have fields dedicated to additional footage for other buildings on the property, such as ADU’s.The other point is that typically, perhaps depending upon location, a space needs to have heating to count in the square footage, which this office doesn’t have if I understand correctly.Consider contacting an appraiser to inquire about how they would handle this space on an appraisal, or a Realtor.

You should check if the bank feeds work with your bank otherwise, it's a deal breaker unless you don't mind manually doing the data entry.

With 4 properties in different location, you have 4 time more chance of RE appreciation.To maximize returns, leverage tax benefits like depreciation, mortgage interest deductions, or cost segregation while considering your ability to handle management demands and market fluctuations.

Turnkey companies usually handle buying and renovating the property, then partner with a local third-party management company to handle day-to-day operations.

Now that we are looking into the next property, we are trying to figure out the best way to handle the financing of it.We don't want to do the HELOC again - it worked the first time, but things have changed and - realistically- we were pretty fortunate that it worked as well as it did the first time.The cabin is was purchased at $230K and it's probably worth around $285K now.

Make sure it can handle the extra capacity before you get too far along.

The barrier to entry is lower so they seem attractive, and to the person who knows what they are doing, they can be very profitable.

It can be difficult and time consuming to find every possible entry point but Section 8 is going to tell you that it's your responsibility to eliminate entry points. 

You can evaluate the additional cost and payback time as if you were paying for heat to get a handle on it but the jump to most efficient is probably not worth it in your situation.