These are good tips!  

Another possibility I looked into is simply leave the current SFH as is since we have long term tenant, but build ADUs on the lot.

Is your tenant month to month or in a long term lease?  

For example, if I send my son money for books, can I do so as a property manager fee so that this is also tax deductible.4) If my son, finds the monthly payment to be to much while he is in school and I end up shouldering some of the costs, how long per IRS rules can I carry a loss on the property.Any help would be greatly appreciated.Thank you.

@Samuel Coronado I’ve worked with a few lending options that have no seasoning requirements and allow you to borrow based on the appraisal or after repair value irrespective of how long you’ve owned the property for.

Finally, be prepared for long timelines and budget flexibility due to the permitting and approval process.Good luck as you grow your portfolio!

I've just heard that from many people over the years.In general, SC is experiencing an economic renaissance, so it is a good time to invest here. 

Do not have this conversation at 8:00 PM on a weeknight after a long day.

Pittsburgh is a good market to make money in now cash flow wise and has good upside as well if you know what you are doing. 

The good news is you don't need a specialty loan for a house hack, just a traditional primary home loan.