Make sure the $5K is not for other third-party fees such as any environmental, title or credit check expense.As for who can order an appraisal, I would defer to an actual appraiser but my understanding and experience is that appraisal regulations only impact regulated groups such as banks and therefore hard money lenders can effectively make up their own rules regarding appraisals since they are not regulated like banks and are lending their own funds.Finally, banks do not have the "right" to redline.

Here's some tips on vetting sponsors / operators you may find helpful.https://www.biggerpockets.com/blogs/9145/53959-vet...

Basically, the mortgage remains in place, with the buyer making the payments.There are scenarios in which this can be beneficial to the seller and the buyer, but this is definitely an advanced strategy that should only be attempted after serious training and using solid paperwork.If you search here on BP for "subject-to" (or "subject to"), you'll find plenty of forum and blog posts on this topic.

When I have a short break, a blog post is always a click away.

Again, the BiggerPockets store has some books for this or you can learn by watching podcasts, reading blogs, and interacting on the forum.

(Have been educating myself mostly through Podcasts,BP forums, blogs, videos, etc.) 

You should use either LLC’s (the old and expensive way) or a Series LLC (the new and more cost/time effective way).

Also how does this effect our landlord insurance?

Everyone kept saying it is hard to comp bc of the second house on the property, but the town considers it single family since the cottage was built before multi family zoning laws were in effect.

Maybe it wouldn't bother me so much if I didn't have to pay taxes on the Martha Stewart effect and those handles cost a more reasonable buck-fifty or so each.