Ultimately, the decision to purchase now or wait depends on your financial goals, risk tolerance, and the specific opportunities you’re considering and every situation is unique, so what works for one person may not be the best for another.

Under 5 units is your pick of what everyone has said above, as each software seems to be quite similar and comes down to personal preference.

Personally, I do not want to leave a future taxable gain to my family. 

Only a few showings, which have gone well, but not one person has actually applied yet. 

Make sure you take the step to transition connections from this forum into in person relationships, building your local RE network.

We can't seem to get people to the property to tour in person or push them past the initial lead.

‘I assume this person is offering 10-15% more than you could get in a regular sale?

Especially if the deals you look at have been on the market for a while and aren't going to have multiple people looking to write on it.You could try having an additional person on your team who's niche is providing boots on the ground services.

They'll probably think it appraised higher but I personally wouldn't want to muddy the water by having that appraisal hanging over the negotiation. 

You don't want to be the person buying the home that didn't sell, even in some creative situation as a new investor.