We are not too strapped for cash, but it always seems better to have more in the bank than less.

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

Quote from @Adam Macias: Wholesaling as it is today will be a thing of the past.It’ll truly be strange to even hear people and gurus trying to make big money off it.The more people try wholesaling but then end up not having an end buyer or cancelling contracts or trying weird things like novations, the more all of real estate will be regulated and cause requirements like licensing to be able to transact more than just your personal resident purchase.Which I don't know why hasn't happened sooner.Here's all the states (in red or yellow) requiring a license to wholesale or at least have started the process:Credit: REITipsterI think licensing and regulation is a beautiful thing that should happen if you plan to be an wholesaler and do more than one deal... which is going to be the case for anyone taking this business seriously.Or even it being regulated to need a real estate agent to do more than one deal outside of buying a personal residence.I've had plenty of failed attempts with agents in pursuit of wholesale deals and I know exactly why, it's not because the agent couldn't find me deals, it's just not practical to think there's opportunity for the numbers a wholesaler needs to make a profit on top of everyone else needing to these days.Because the only sellers who truly can sell at a deep enough discount are usually those who ran out of time and just didn't do something sooner with their situation.I know many coaches and gurus will disagree with me but there’s no regulations on youtube gurus and what they teach either.If we look at the current state of the market in hot cities, the availability of online resources to the average homeowner, how many deals can you possibly believe are available at 70% of ARV?

Note this election MUST be made in the year of the dispositions.2) 1031 - There's usually no tax on gains or losses when swapping property for similar property.

The itemized damage estimate that my insurance provided me lists an Actual Cash Value that is 15% higher than my Dwelling A Coverage. 

(Compared to the usual 30-40 year path.) do they think people with a million or millions in stock just got there?

Quote from @Ko Kashiwagi: Hi Donyea,Love the Birmingham market and I've worked with a couple of agents there.

The IRS doesn't trust you to report accurate information, so the 1099 from the property manager is checked against your filing.Any company that does more than $600 in business with you should issue a 1099.

With the future being so uncertain I realized there was a need to do more than just rely on my job for financial security. 

Illinois is a great market, but I agree with most that it would be much easier if the investment were closer to you.