I have several LLCs I use for my real estate investment business. I want to designate one--let's call it "LLC-S"--that I use for short- term deals to be taxed as S corp, since I pay ordinary income tax rates on those deals anyway. But I cannot really deduct non-basis expenses (like travel to properties, some are far away) related to those on a Schedule E like I can for my rentals, so as of now, I just don't deduct them at all. If I file IRS 8832 today, am I still able to deduct expenses (like the pricey seminar I attended in November) relating to "LLC-S"s activities that occured earlier this year or even in previous years? These are expenses I haven't figured out how to deduct. My CPA is no help, she just plugs my numbers into her software and gives me the results, and won't advise me (yes, I know, I'm shopping for a new one now).
Once so designated, can my "LLC-S" buy health insurance (an HSA?) for me, or is that deduction only for C corps? I understand insurance may be counted as income to me. What kind of retirement benefits may be deductible to "LLC-S" if I put $ into a retirement fund (IRA? 401k?) for me? What if I hire my wife (or even make her a partner in the LLC), can I deduct her insurance too, and/or have "LLC-S" contribute to her existing IRA?
Finally, I have a couple of recently-bought properties I want to deed into "LLC-S" before I sell them. Should I do that before or after I elect S corp taxation from the IRS via form 8832? Any advice is much appreciated, thank you!