I can tell, right here, right now, that Austin is the worst major metro to invest in rental housing stock in 2024.

Literally everyone is a RE coach or some type of finance expert (typically buying stocks/index funds some crypto) and they talk on and on about "contact me about how to be successful and free from your W2 job.

My goal is to reach financial freedom as quick as possible. Which would be done by using the cashflow from RE properties. I am trying to figure out if I should also max out my own personal Roth IRA in the S&P or j...

You are providing the seller a convenience1) The deal will not fall through because of financing contingency2) You can close faster than those neeeding financingIn exchange, the seller gives you a reduced price.

You can exchange ideas with your agent and have him work something out with the other side through conversations but once you all agree on a plan you MUST GET IT IN WRITING so everyone is legally bound and your EMD and interest are protected. 

I would recommend finding someone in your market who is already flipping and being a resource to them in exchange for knowledge.Wholesaling is a completely different business, with 80% of it being marketing and sales.

And if they are, and you have not sold your property interest, explore common strategies like 1031 exchanges.

He can answer some of the logistics in a 1031 exchange. 

“Genius” me agreed to rent a house for them in exchange for fostering a few of my dogs (I run a dog rescue group.)

There are specific rules for 1031 exchanges including:The replacement property must be identified within 45 days of transferring the relinquished property.The replacement property must be received within 180 days after the transfer of the relinquished property or the due date of the taxpayer's tax return, whichever is earlier.Special rules apply for exchanges between related parties (defined in § 267(b) or 707(b)(1)).Real property located in the United States and real property located outside the United States are not considered property of like kind.Cost Segregation StudiesA Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.