Company B's 401(k) balance can be penalty free after you attain the set age or if you're separated from its service.Joint Committee on Taxation: General Explanation of the Tax Reform Act of 1986 (Actual Internal Revenue Code ("IRC") does not have this same exact language but this report shows the intention of Congress when drafting the IRC at the time)Page 717: "The exception for payments under a plan after separation from service following attainment of age 55 continues to apply if the employee returns to work for the same employer (or for a different employer) as long as the employee did, in fact, separate from service before the distribution."

Furthermore, your profile mentioned 'fix and flip'.if you acquire some rentals, you may benefit if you can claim real estate professional status.There are a couple of CPA's here on biggerpockets that specialize in real estate taxation.

If so, there are 20+ accountants on this site that specialize in real estate taxation. 

@Brad Van Rassel You are in a great area Brad,With metro Nashville and Davidson county’s tax drama.Starting around the city are all great areas.I am in Columbia and rehabbing ,but also watching for great rentals.Ours cash flow as well as MtJuliet,Murfreesboro,Clarksville and any area around the metro.Until Google and Amazon head quarters are done in Nashville that market is going to be crazy.Now that the hotel counts are increasing the VRBO and legislation to stop VRBOs are going to decline IMO.Best Of Luck!

I really like that they do quarterly walkthroughs in the property and take pictures. 

im trying to avoid double taxation, but also collect profits...  

So basically if it's the same type of property and taxation together if it's different then it gets its own accounts.

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

I'd prefer for them to be billed and pay it directly, but the last tenant I had in one of the houses (ended up being evicted), didn't pay the last quarterly bill. 

Consider 50 dollar a month increases until you get to market rents or quarterly increases over the next year.