Tax questions and SSI payments

[Molly L.]

Hello all you smart people......I have been a stay at home mom (my husband works a 7-5 government job) and commercial real estate investor for the last 20 years.  Every year I discuss our return with our tax preparer on maximizing our return.  I have asked him several years in a row, how do I pay into Social security and Medicare?  Every year he tells me, "Don't file in the way to pay into either program.  That it is not a good plan."  So, I don't. 

Next year my husband wants to quit working at his main job and take a year off and then do a new job for fun. (He is 53).  I will continue to run our commercial real estate property management company as long as I can and have interest, most likely. It is parttime work about 10 hours a week, sometimes more when I have repairs or remodeling.  I have 10 units.  

My husband and I have been running the retirement numbers, and while I understand my SSI can be half of his when we claim in the future.....the real heartbreaker is the medicare cost for me.  It will be around $450 for part A per month, plus the costs for part B $150 now I think too.  Is there a way to pay into the system by filing my business as a Schedule C instead of Schedule E?  How does this affect me year to year?  Who can I discuss these questions with? My dad has been a commercial RE investor for 50 years.  He said he paid into SSI and receives benefits now. He still runs his business with help at age 78.

Finally, how would my business need to structured for me to claim unemployment if this covid thing keeps going?

If I structured my business as income, couldn't I shelter most of the income one of the IRAs for self employeed people?

My tax returns are done for 2019. Our income is 91k husband, 6500 ord div, 3300 qual dividends, 73k business income, 3 kids ages 13,18,19; husband maxes out 457(25k) and Roth (7k); I max out trad IRA (7k)...standard deduction 24.4k and business dedcution 14.6k I owe 19.7 in taxes.

Thank you!