Depending on your other income, short-term vs. long-term strategies can have very different tax implications, and many people get into real estate investing precisely because of how it interacts with their overall financial picture.Since you guys are planning flips now and rentals later, the tax setup matters more than most people realize.For flips, the IRS treats everything as active income, not capital gains, so once you’re doing more than a deal or two a year, you’ll want an S Corp (or LLC taxed as one) to avoid paying more self-employment tax than you need to.

Are you investing as a family, partner, or is this a business/corporation? 

They are typically started out as corporations that once they hit reach reit status will turn into a reit.

On Oahu, you get plenty of travel nurses, corporate stays, military orders, insurance displacement, and remote workers coming for 1 to 3 months.It’s not as sexy as nightly, but cash flow is often steadier and the regulations are clearer in many areas.If you’re set on luxury STR, just make sure the zoning and HOA truly allow it and underwrite using real seasonality.

Are you investing as a family, partner, or is this a business/corporation?

Another option could be a corporate or insurance housing provider that offers longer placements without frequent turnover.If you’re open to passive models, a Co-Investing Club im in has members who’ve partnered with experienced operators for steady, hands-off returns without the tenant headaches..worth exploring if you’d rather redeploy your equity than re-tenant.

To clarify for those reading the company is Prime Corporate Services out of Utah.

Starting with flips to build capital and then moving into buy-and-holds makes sense, but you could probably get into long-term rentals now if you find a property with potential that just needs minor improvements, especially if you’re balancing a full-time W2 job.From a tax perspective, the main thing to understand early is that flip income is taxed as ordinary income, not capital gains, since it’s considered non-passive business income.

I only lend to LLCs or corporations, and the property has to be a true investment asset.The reason is once it’s an owner-occupied home, consumer-lending laws kick in, and the compliance requirements are totally different.

The revenue looks like the following:Football Weekend House Rentals: $32,000 (8 home games × $4,000 per game for full house rental during game weekends)Short-Term Airbnb Rentals: $47,952 (333 non-game days × 48% occupancy × $300 nightly rate for year-round vacation/corporate rentals)Game Day Parking: $9,000 (8 home games × 15 parking spots × $75 per car for tailgaters walking to stadium)Total Annual Gross Revenue: $88,952Looking for input on the following:1.