All Forum Posts by: Cole Bossert

You don't need a separate LLC for each property, but whether you should depends on your risk tolerance, portfolio size, and management preferences. Some investors do a one LLC per property strategy to limit liability—if someone sues over one property, they can't go after the others. However, this also means multiple bank accounts, tax filings, and admin work, which can be a headache.

If you go that route, some investors use a holding company (often a parent LLC or even a trust) that owns all the separate LLCs. This can provide additional asset protection and streamline management. That said, if you only have a few properties, keeping them under one LLC (or a couple, if you want to separate asset classes or locations) is often more practical. A good attorney or CPA can help you decide the best structure based on your long-term goals.

For a beginner wholesaler, the key to knowing if a property is a good deal is making sure you're getting it at a deep enough discount so an investor can still make money after buying it from you. A simple way to check is using the 70% rule—investors typically want to buy at 70% of the after-repair value (ARV) minus repair costs. If a house is worth $200K fixed up and needs $40K in repairs, an investor won't want to pay more than $100K. That means you need to get it under contract for less than that to leave room for your assignment fee.

Once you find a deal, make sure your purchase contract includes an inspection period so you have time to find a buyer. You’ll send the contract to a title company that works with wholesalers (some don’t), and they’ll check for any title issues and handle closing. Before signing anything, make sure the contract allows you to assign it to another buyer—otherwise, you could get stuck with a deal you can’t move.

You’re in the thick of it now, and this is exactly where most first-time investors hit that wall of frustration. But the fact that you’re making offers, going under contract, and walking away when the numbers don’t make sense means you’re doing it right. The competition is tough, but persistence is key. Every deal you analyze sharpens your skills, and every contract—whether it closes or not—teaches you something valuable.

You’re referring to the Section 121 exclusion, which allows you to exclude up to $250K in capital gains ($500K if married) if you’ve lived in the property as your primary residence for at least two of the last five years. However, since your properties were rentals, only the portion of the gain attributable to appreciation is eligible for exclusion—any depreciation you’ve taken will still be subject to recapture at a 25% tax rate.

The biggest pitfall is the inconvenience of moving multiple times and the potential loss of rental income while you occupy the property. Also, if the market shifts and values drop while you wait out the two years, you might not come out ahead. If you’re really looking to defer taxes, a 1031 exchange could be another route, rolling your gains into another investment property rather than cashing out. It just depends on your long-term strategy—whether you want to cash out tax-efficiently or keep growing your portfolio.

It depends on your priorities. A full-service realtor will typically get you the best price and handle everything—marketing, negotiations, paperwork—making the process smoother. Companies like Clever can save you on commission fees, but you may not get the same level of service, marketing exposure, or negotiation expertise. If your main concern is netting the most money, consider interviewing a few agents and negotiating their commission. A good agent can often make up for their fee by getting you a higher sale price. Are you in a hot market where homes sell quickly, or do you need a strong marketing push?

You’re thinking in the right direction, but foreclosure auctions come with a few big risks that can eat into those numbers fast. First, many auction properties are sold as-is, meaning you can’t inspect them beforehand. If there’s major structural damage, liens, or unpaid taxes, those become your problem. Second, there’s competition—bidders with deep pockets can drive up the price, making it less of a deal than it initially looks. Lastly, if the property is occupied, you may have to go through eviction, which adds time and cost. If you’re going this route, make sure you dig into title research, understand local auction rules, and have a solid plan for hidden costs. Have you looked into getting access to off-market deals before they hit auction?

AI is definitely making a big impact on real estate marketing, especially for automating things like listing descriptions, email sequences, and ad copy. It speeds up content creation and helps personalize outreach at scale, but pure AI-generated content still lacks the human touch needed for relationship-building and nuanced persuasion. The best strategy is a blend—using AI for efficiency and data-driven insights while layering in human expertise for emotional connection and brand voice.

If it’s been sitting that long, the market is telling you something—either the price is too high, or the demand isn’t there for that type of rental. Have you checked comparable rentals in the area? Even a $50–$100 drop can make a big difference. Also, are you offering any incentives, like a free month or reduced deposit? Section 8 could be an option, but it comes with its own pros and cons—more guaranteed income but also more red tape. If you’re set on market tenants, you might need to tweak the marketing, refresh the listing with better photos, or even consider a property manager to help get it filled. Have you had any showings or feedback from potential renters?

A lot of these are institutional investors, hedge funds, or large investment groups packaging multiple properties under one LLC for liability and portfolio management. Some are also wholesalers or syndicators structuring deals this way for easier transfers. I've got a buddy who LLCs each property individually and just names them after the address—keeps it simple and clean for bookkeeping and liability separation.

Buy & Hold is still one of the best long-term strategies in 2025, but like any approach, it depends on your market, financing, and risk tolerance. With interest rates fluctuating, affordability challenges, and shifts in rental demand, investors need to be more strategic than ever. In strong rental markets with job growth and population increases, Buy & Hold remains a solid wealth-building strategy, especially if you lock in good financing and optimize cash flow. However, short-term strategies like value-add flips, BRRRR, or even mid-term rentals might offer better returns in certain markets.