Hi @Austin Walters,
I have been licensed for a total of 5 years, and have been wholesaling for 3 of those. Granted, I am in Washington State, and it sounds like we have some different laws regarding the practice. What I would do is talk to a real estate attorney that comes highly recommended, and pay them for an hour of their time to ask those tough questions.
I can tell you from my experience doing both, I haven't had any bad repercussions (YET!). But you do need to put contingencies into your PSA docs to get you out of deals that do not fit your buying criteria. I write my deals up in my LLC with and/or assigns. I put a earnest money promissory note (an MLS form) in my PSA's, so there is no deposit until AFTER the inspection is approved. If you are doing a direct mail program, I would make sure you have permission from your managing/designated broker that you can do that, and keep it on file. Here in WA state, we put in our letters for the seller to forward the letter to their broker if the property is listed already, since that happens from time to time....
Hope that helps! But for sure, have a real estate attorney spell out what you legally can and cannot do...! Its worth the $$$. Cheers!