I currently own one home that I’m house hacking, and want to continue to pick up homes with owner occupied financing as time and money permits, but also want to get into bigger deals with more units.Thank you

When I want something completed in a hurry I get permits and as much of the materials as reasonable stored nearby and make sure of contractor schedules, and don't rely on people you have not used before.

Make sure if there is a permit required for the vacation home you are purchasing, that it is transferrable. 2.

You have to read the ordnance, but typically there is a ‘permitted use’ which is the zoning class, then there are ‘prohibited uses,’ and in between there may be some combination of ‘’conditional uses’ or ‘performance standards’ where you can potentially use it for another authorized purpose.

I didn't find any permits related to that in the records so it might've been done without permit.

There is no limitation on the total number of like-kind replacement properties. 95% Exception You may need to identify significantly more like-kind replacement properties than the first two identification rules permit.

It sounds like this might a good time to look for buy & hold properties that already have a (permitted) ADU, since they will be somewhat undervalued using current appraisal methods.

Make sure to properly vet the prospective tenant to ensure you would rent to them under normal circumstances. 

-Building permit can be acquired for only permit fees, structural engineering, soils testing and surveying fees.

You should always consider apartments as an option for your prospective tenant, because if it costs them more to make payments on a mobile home plus pay the lot rent, they could just rent an apartment instead.