A couple questions and thoughts that have came across my mind are below.Contributing factors: (My goal like most newer investors is to reach financial freedom)-Area: Western Suburbs of Chicago.

New tax rules are at the core of President Biden’s ambitious economic plan, “American Families Plan” that calls for $1.8 trillion in spending and tax-credits for provisions, The most prominent impact of the plan on real estate is the treatment of capital gains.

However I see that if you can structure this deal correctly you can qualify for a long time capital gain.Tips to get capital gain treatment on the sale: A) If you have actual investment property and you are dealer: -Maintain separate book-Document intent to hold the property as investment property in Minutes or other document-Report expense as investment expense on tax return-Also use separate entities.Using controlled entity to get capital treatment on land:-it is important that the sales price reflect the property's actual FMV at the time of sale. the formalities of a sale must be observed.

Then you need to factor in the cost to finance if you are doing so (ie. underwriting fees, closing fee, etc.), holding costs (utilities, property tax, etc.).

In my experience flippers make the quality of a city improve, but like @Greg H. said, there is the "you aren't from around here" factor at play.

If you purchased a property, significantly rehabbed the property and immediately sold it thereafter with the intent of flipping it, it will be subject to self-employment taxes.Regarding the taxes you will be subject toFederal TaxesState taxesDepending if it was a flip or not, also self-employment taxes.Speak with your accountant on the actual taxes that will be due as he/she will know what your marginal tax rates are.You can also factor in improvements / selling costs to decrease your gain / taxes.

I did more research and thinking after I posted and I determined that I am likely eligible for the primary residence exemption on taxes which negates the capital gains factor.

You can even split that into multiple properties if the cashflow numbers make sense.On the smaller factors side - $300 HOA IMO is down the drain which is one of the reasons I like to avoid Condos.

(The seller offers the tenant anywhere from $3k - $5k in cash for keys) This can be factored into the price or negotiated with the seller upfront so it is amicable to both buyer and seller.We cannot bend the 60 day move in rule because it is a HUD/Fannie/Freddie requirement for occupancy post close.

Walking distance isn’t really a factor since most people have cars.