Being trapped in a non-cash flow generating asset is not investing.

The questions I have are....What methods of lead generation has been the most effective for you in Cleveland?

Now, I could have decided to buy the property with the SFR and the back unit as a rec room and simply rent it out to one large multi-generational family - and that would have been certainly legal.  

I want more experienced real estate investor’s guidance, opinions and ideas on how to go about it.Below are some of the tasks that I am planning to undertakeFinalize a state/county/city/Neighborhood – How to I arrive on an area (GDP, Population, Employment, real estate growth or any other criteria) ?

Overall you want to make sure your properties will generate enough to cover at minimum the expense of owning them which means to pay for maintenance, insurance, and upgrades if necessary plus cover the cost of finance, loan and interest payments, and property taxes which you as the owner will be liable for. 

All the people I know who are generating rental income in DC/Montgomery/Howard area bought a long time ago.

Often times tenants have divorce, car accidents, loss of employment and health issues.One of the things landlords have to be careful about is tenants want to make their problems the landlords problem.First your want to let her know that you are truly sorry that she is having medical problems.If you are wanting to waive some of the rent is totally up to you, but you do need to remind her that she still has financial obligations and needs to see what arrangements she could do to have the rent paid right away.If you have any emergency contacts for her on file youu may want to check with them and see if they are able to help her.I would also recommend that you get a real estate attorney that is familiar with evictions and consult with the attorney.

The initial investment was low, and is generating almost 30% ROI annually.  

Originally posted by @Stephen Chittenden:You can use some strategies (such as 1031 exchanges) to defer taxation, but otherwise the profit on each flip will be subject to taxes.You can't do a 1031 on a flip property...In general, all flip income will be subject to ordinary income taxes at your marginal rate, plus self-employment taxes. 

It sounds as if this 401k is with your current employer, so you likely do not have the option to move that to a self directed IRA.