Spring is best time to sell, I had 13 offers on my last home in first 48 hrs, and saved >100k, why give away your hard earned equity that you took the risk on?

Essentially, I'm holding onto this property for myself and dipping my toes into landlord responsibilities in the interim.However, I'm now unsure if I'm taking the best route, as despite aiming for breakeven or positive cash-flow, the house isn't attracting any applicants.

But you can still treat it as resulting in Ordinary Income even though it is reported on Schedule E, which lets you properly report in accordance with the tax results it seems you are shooting for under the tax return loophole.If your CPA is looking at switching it between schedules to get that tax result...it sounds like they don't understand the reporting position fully and/or they just don't know how to use their own software to address it.In summary, based on what you are describing for the situation, it should go on Schedule E, with what sounds like the resulting refund of $17k.

If I lend 30k for someone to close a REO deal then I'll have their car pledged, or have a co-signor that pledges the 30k if it is defaulted.a 2nd lien position with no protection is like going to Vegas and betting on black, only on that bet you win 30k, in a 2nd lien position what do you stand to make on a 30k short term loan? 

Yes, some locations are better than others but it all comes down to price, condition & what you can get in rental prices to ensure you have both income & equity in the property you are buying. 

One other way is to generate passive income from something else, such as cash-positive syndications.

This benefits today’s buyers, because there is less competition for the current supply of houses in the market and it puts you into a better position to get the house that you like and want.

To be honest, on over 100 building permits last year in the City of Chicago, with many of them having some form of enclosed porch, I think only 2 were ever mentioned by the Department of Zoning where they brought it up as a "Concern" which led us on a wild goose chase of finding and sharing information, overally causing unnecessary delay to the permit review process and eventually coming to a close (some positive, some negative).

Im struggling because I do have one of the nicer looking homes in the area and a-lot more amenities but in my position I dont really want to take some major risk going into high season and missing occupancy.

On another note about the area, very positive news about Sony Studios project/mixed-use development.https://www.reviewjournal.com/business/1-8b-sony-movie-studi...