Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

I've heard that some people have used a trust account or something similar as a method of income, if you can prove history of payments and continuation of these payments.

Flexibility is key for me as I navigate opportunities and continue learning.I’d love to hear any advice you might have or discuss potential opportunities if you’re working on something similar.

You could likely get into a rental with a DSCR loan at 20% down, which would be similar or less in terms of DP on an owner occupied loan via conventional financing in eastern MA. 

Where I differ with most of the posters on this thread is that I feel solutions can be developed to address the problems and something similar to what the OP suggests would be viable. 

Hey @Sundone Boutvyseth,Similar to what @Brad Jacobson said, your best option might be a secondary residence loan if you want to STR.

Unfortunately cap ex usually catches up to them and the appraised value rarely translates to a similar sale experience and all along the property has merely been a highly levered property.

You need your house rules to say no more than XYZ people, and no guests count over the number in the listing between 10:00 PM-6:00am or something similar.

Your son is likely paying more than the property is worth, by definition, as the seller would almost certainly prefer a similar offer that was not subject to. 

I have seen other similar homes rent for $2,200 - $2,500.I appreciate any advice from this very helpful community!