It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.

To maximize returns, ensure compliance with local regulations, prioritize owning the land, and offer student-friendly amenities.

Question for any and all.. we have had trouble finding a real estate investor friendly CPA, one that proactively wants to help us learn and obtain all the tax rewards with real estate. 

Quote from @Mathew Chacko: Hi friends, did anyone end up using e1031xchange ?

Hi Kemi,I’d recommend connecting with investor-friendly agents and wholesalers, as well as joining local Facebook groups for off-market deals.

and even for friends and family, that's more of a favor than a loan...you asked not to sugarcoat, so here goes. 

Plus, compared to other parts of Florida, the Panhandle is still relatively affordable, making it a great option for first-time investors or those looking to diversify their portfolio.Another huge perk is Florida’s no state income tax and landlord-friendly laws, which make it easier to manage and profit from rental properties.

Definitely connect with an investor-friendly agent, they should have all the knowledge, resources, and connections you will need.

A Realtor friend said he had some of his busiest years during that time so life goes on.

If that is the case then I would say yeah work with an agent who has a solid reputation either here or from a friend referral.