You do need to classify any income you receive that you want to contribute to the 401K as ordinary income.

Go to your county web site and they should have a link to the monthly tax auction on the courthouse steps.  

I was initially planning to hire some contractors to get the work done, then find a property management company to find and manage tenants.It would be helpful for me to understand the following:(1) I don't want to be classified as an active real estate investor in front of the IRS.

@Shawn Carrie Sounds like you're ahead of the herd my friend, networking is key, attend some local REI group meetings, call around to mortgage "brokers" get to know them let them know your business plan, hit up local community banks, type "hard money lenders (your city)" in a web search and call them for bridge loans etc.

I'm easily found in a web search.Bill

So, for example, you have been STR a property successfully for say 3 years, AND are not reliant on a third party marketer like Airbnb, in other words have repeat renters and a strong transferable web presence.  

Some counties are still not "digital" or at least if they are they're not web-accessible or aggregator-friendly.

Hello @Michael Plaks and @Ashish Acharya, are you allowed to change/switch the category of your engagement to the property from Passive to Active participant in the future once you classify them when you acquired the property?

Most of this stuff you could look up yourself using free resources on the web.  

@Chris Kendrickyou are CORRECT that many of the methods you mention are much more difficult than they are presented as being on the web and on podcasts and whatnot.