Not exactly sure how this would work to make sure we are taking advantage of the loss reported for our own personal taxes.

I get the feeling you aren't paying taxes on your unreported income, which is against the law. 

If I am transferring 2 properties from a co-owned LLC to a personally owned S-corp, do I have to pay any taxes on that transfer?

I am a licensed realtor here in Los Angeles, don't want to deal with the exodus of insurance companies and difficulty getting insurance and keeping it after a claim, tenant landlord laws being heavily in favor of tennants, exorbitant property taxes and minimal RTP among a few other factors with these being the most inspiration to take my money out of california.  

@Hector MejiaNevada is a great state to invest in because it's landlord friendly, no state income tax, lots of job growth, and positive population growth. 

Tax benefits?

From the law, I see that since I didn't give them a copy of the checklist, the security deposit is not "legal".

I’m an engineer that makes a little bit over 100k before taxes and my credit score is 688.

My 250K tax benefit will run out before his lease does on the 2 of 5 rule, so it might be a good time for me to sell - and help him with a lower rate than banks can give while giving me income until he refinances.

Should be fairly straightforward You know the cost you'll pay for the property The rate and term (ex 7% for a 30yr fixed)Property taxes - this can be looked up via https://atlas.phila.gov/(If you are house hacking you van take advantage of the $80k homestead reduction)Insurance - this may be a bit tricky unless you reached out to a broker already Is there an HOA?