It really depends on your situation.

I recommend being more specific, consider the number of comparable rentals, not just the total number of rentals.If your rental is $2000/month and you see rentals at $3000/month with long time on market, that is interesting but not as directly relevant to your situation.

Given your situation and interest in potentially expanding your investment portfolio, you might consider the BRRRR method as a strategic approach.

Here is our situation: we downsized about 2.5 years ago to a house that we had planned to rent out, we have about 36k in a HELOC that we can use right now to either buy another house to move into or put into an investment property.

I have long wondered if transferrring title to an LLC while keeping the loan in the borrower's name personally could open the door to a piercing the corporate veil situation.

For me doing this OOS didn't work, far too stressful being 2000 miles away, can't check on the renovation each week and ARV wasn't high enough so I bought move in ready in Indiana. 

Two options-tell them to move and not renew their lease, or see if them paying 50% of the rent on the 1st and 50% on the 15th would work better for them-stressing that it must be paid on time (do a 3 month trial) or you are simply not going to renew their lease.

Let's delve into the situation you've outlined:If your rental income exceeds the 27.5 years of depreciation and deductions, resulting in a positive net income, you are correct that this surplus becomes taxable income.

Everything is highly individualistic and there isn’t a “right or wrong”, but what works best for you and your situation. 1) what is your ultimate goal for your ideal investment property?

Hope this helps - sugar coating your situation doesn’t help you at all.