Skip to content
Get Started
Resources & Media
Resource Hub Bookstore Blog Guides Pro-Exclusives PRO Podcasts Pro Partnerships Property Management Toolkit Newsletter NEW
Events & Training
BPCON2025 Webinars Bootcamps Upcoming Events Free Courses
Strategies
How to Manage Your Rental Property How to Operate a Short-Term Rental How to Passively Invest in Real Estate How to House Hack How Does the BRRRR Method Work How to Flip a House How to Invest in Commercial Real Estate How to Invest in Real Estate How to Invest in Multifamily Real Estate How to Build Wealth
The BiggerPockets Conference
This is your chance to learn from the best, network with the best, and become one of the best in the game.
The Podcast Investors Trust
No fluff. Just deals, strategies, and lessons from the front lines of today's market.
Pick Markets
Pick Markets
Market Finder - NEW PRO Picking a Market Workshop PRO Picking a Market Worksheet Top 100 Cash Flow Markets Market Insights - Sunbelt Region
Market finder
Pinpoint the best real estate market for your specific goals with expert recommendations and real-time data on appreciation, affordability, rent-to-price ratio, and more.
Pro membership
Get unlimited access to tools and resources that make it easier to find, analyze, and manage deals with confidence!
Find Deals
Find Deals
BiggerDeals NEW Off-Market Deal finding PRO Real Estate Syndications Investor-Friendly Agents Find Foreclosures Community Listings (FSBO) Business Directory
NEW! Find Cash-Flowing Deals Fast
Search nationwide listings with built-in cash flow analysis.
Invelo - off market deals
Scale your portfolio with off-market deals.
Analyze Deals
Calculators
Rental Property Calculator PRO Rehab Estimator PRO Rent Estimator PRO BRRRR PRO Fix & Flip PRO Short-Term Rental PRO Sell vs. Keep PRO Landlord Insurance Calculator by Steadily All Calculators
Rental property calculator
Is it a good deal? Run your numbers like a pro with this simple yet powerful calculator.
Rent estimator
Understand how much rental income you can expect based on recent reports and data for your specific property.
Manage Properties
Manage Properties
Managing Properties 101 Find a Property Manager RentRedi Property Management Software PRO Baselane Banking and AI Bookkeeping PRO Property Management Tools Ask a Management Question Finding Tenants Screening Tenants PRO Leases + Landlord Forms PRO Accounting/Bookkeeping PRO Property Insurance Property Maintenance / Rehab PRO
Property management software
Manage tenants, tasks, and your entire portfolio with one simple tool.
Property manager finder
Find reliable property management partnerships that last.
Pricing
Plans & Pricing
Pro Membership Business Membership
Try PRO for 7 days completly free
Avoid mistakes and make informed decisions with Pro.
Grow your business
Promote your business on BiggerPockets and make quality connections with the right investors.
Forums
For You
Newest Trending Unanswered My Discussions Followed Discussions Followed Categories Followed Locations Followed People
General Real Estate
General Real Estate Investing Starting Out Deal Analysis Buying & Selling Business & Marketing Landlording Property Management Reviews & Feedback
Real Estate Strategies
House Hacking BRRRR Short-Term Rentals Mid-Term Rentals Multi-Family Fix & Flip Other Strategies
Finance & Financing
Lending Creative Finance Personal Finance Taxes & Legal Issues
News & Announcements
Official Site Announcements Market Trends & Data Real Estate News & Current Events Pro Exclusive Area PRO
Events & Networking
Events & Meetups Classifieds
Store
All Books
Best Sellers Browse All New Books & Pre-Orders Bundle & Save Books for Beginners
Flip your way to financial freedom
Scale your investment framework with this valuable guide to compounding real estate success.
Outsmart the short-term rental competition
Cash in on the exploding STR market with this must-have guide from expert Avery Carl.
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime
×
Take Your Forum Experience
to the Next Level
Create a free account and join over 3 million investors sharing
their journeys and helping each other succeed.
btn_google_dark_normal_ios Created with Sketch.
Continue with Google
Continue with Apple
Use your real name
By signing up, you indicate that you agree to the BiggerPockets Terms & Conditions.
Already a member?  Login here
Followed Discussions Followed Categories Followed People Followed Locations
Short-Term & Vacation Rental Discussions
All Forum Categories
Followed Discussions
Followed Categories
Followed People
Followed Locations
Market News & Data
Market Trends & Data
Buying & Selling Real Estate
Out of State Investing
Real Estate News & Current Events
Real Estate Technology
Investor Mindset
General Info
BiggerPockets Exclusive PRO Area
PRO
General Real Estate Investing
BPCON
New Member Introductions
Questions About BiggerPockets & Official Site Announcements
Off Topic
Starting Out
Real Estate Success Stories
Real Estate Horror Stories
Real Estate Strategies
House Hacking
Commercial Real Estate Investing
BRRRR - Buy, Rehab, Rent, Refinance, Repeat
Mobile Home Park Investing
Innovative Strategies
Multi-Family and Apartment Investing
Land & New Construction
Wholesaling
Rehabbing & House Flipping
Short-Term & Vacation Rental Discussions presented by
Tax Liens & Mortgage Notes
Medium-Term Rentals
Buying & Selling Small Businesses
Outdoor Hospitality
Landlording & Rental Properties
General Landlording & Rental Properties
Managing Your Property
Marketing Your Property
Tenant Screening
First-Time Home Buyer
Real Estate Professionals
Mortgage Brokers & Lenders
Contractors
Real Estate Agent
Financial, Tax, & Legal
Creative Real Estate Financing presented by
Personal Finance
Private Lending & Conventional Mortgage Advice
Insurance
Tax, SDIRAs & Cost Segregation presented by
Foreclosures
1031 Exchanges presented by
Goals, Business Plans & Entities
Legal & Legislation
Real Estate Classifieds
Classifieds
Real Estate Events & Meetups
Reviews & Feedback
Ask About A Real Estate Company
Real Estate Deal Analysis & Advice
Guru, Book, & Course Reviews
Syndications & Passive Real Estate Investing

Updated over 2 years ago on . Most recent reply

Wesley Myers's profile image
Wesley Myers's profile image
Wesley Myers
  • Rental Property Investor
  • from Inlet Beach, FL
  • Member since Oct 10, 2019
Connect

User Stats

90
Posts
32
Votes
Wesley Myers's profile image
Wesley Myers's profile image
Wesley Myers
  • Rental Property Investor
  • from Inlet Beach, FL
  • Member since Oct 10, 2019
Connect
Wesley Myers
  • Rental Property Investor
  • Inlet Beach, FL
32
Votes |
90
Posts
Short-Term & Vacation Rental Discussions

Healthcare insurance with your STR business?

Wesley Myers
  • Rental Property Investor
  • Inlet Beach, FL
Posted

Looking to the future with the goal in mind for managing my rentals vs working a W2 job with benefits what are you doing for healthcare insurance?

My current state job has great insurance for our small family of 3 but one day I envision this changing once we reach enough properties. 

How are you handling this? 

0 Votes
Follow
6 Replies
Jump to Last Reply
Log In or Sign Up to Reply

Most Popular Reply

Leslie Anne Morris's profile image
Leslie Anne Morris's profile image
Leslie Anne Morris
  • Real Estate Agent
  • from Smoky Mountains, TN
  • Member since Mar 27, 2022
Connect

User Stats

1,261
Posts
982
Votes
Leslie Anne Morris's profile image
Leslie Anne Morris's profile image
Leslie Anne Morris
  • Real Estate Agent
  • from Smoky Mountains, TN
  • Member since Mar 27, 2022
Connect
Leslie Anne Morris
  • Real Estate Agent
  • Smoky Mountains, TN
982
Votes |
1,261
Posts
Leslie Anne Morris
  • Real Estate Agent
  • Smoky Mountains, TN
Replied

COBRA for 18 months - then you'll need to find a health care broker to bid out for a new policy.

1 Vote
Log In or Sign Up to Reply
Sort By:

Loading replies...