If the activities rise to the level of a trade or business and you/the entity are/is a dealer with respect to the mentioned properties, the income would not be capital gains but instead ordinary trade or business income subject to SE taxes.I'd recommend you engage a professional to help make the decision (especially if you expect first year net to be $300k), as there are qualitative and quantitative factors that need to be considered. 

Once you get the relationship established, stay in contact with them.

Just need to establish rules in place prior to renting out rooms. 

You aren't going to get past it, its well established in PA that transfers between individuals & LLCs triggers the transfer tax.

The issue is that the newbie's value could be off or the inspector could find a large issue (I had one inspector find a $30K problem and we found a $45K problem).Waive of contingencies is best left to those with significant experience and/or that were not planning on using conventional financing.In addition, the appraisal basically establishes retail price. 

Have you started establishing the Deal Flow and Execution legs yet?

Treat all people with respect 

The new document https://www.hud.gov/sites/dfiles/PA/documents/HUDAsstAnimalNC1-28-2020.pdf spells out best practices for property managers and landlords with respect to assistance animal requests.I hope this will provide you with more info on how to determine if the animal is qualified and how to screen tenants Cheers, Yuriy 

So my primary question would be: is there a particular avenue to establish the seller financing or is it all done via lawyers?

A lot of forum members are very knowledgeable in their respective fields related to real estate investing, whether that is real estate sales, wholesaling, flipping, rentals, lending, self-directed IRA and Solo 401k investing, or tax and legal guidance.